- The discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine cannabinoid type 2 receptor agonist
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The development of selective CB2 receptor agonists is a promising therapeutic approach for the treatment of inflammatory diseases, without CB1 receptor mediated psychoactive side effects. Preliminary structure-activity relationship studies on pyrazoylidene benzamide agonists revealed the -ylidene benzamide moiety was crucial for functional activity at the CB2 receptor. A small library of compounds with varying linkage moieties between the pyrazole and substituted phenyl group has culminated in the discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine agonist 19 (CB2R EC50 = 19 nM, CB1R EC50 > 10 μM). Docking studies have revealed key structural features of the linkage group that are important for potent functional activity.
- Moir, Michael,Lane, Samuel,Montgomery, Andrew P.,Hibbs, David,Connor, Mark,Kassiou, Michael
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- A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones
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The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KOt-Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O-unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a catalytic amount of isopropanol, or 18-crown-6, was necessary to facilitate the reaction and to reduce side-product formation under ambient conditions.
- Pienaar, Daniel P.,Butsi, Kamogelo R.,Rousseau, Amanda L.,Brady, Dean
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supporting information
p. 2930 - 2935
(2019/12/23)
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- Microwave synthesis of 1-aryl-1H-pyrazole-5-amines
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A microwave-mediated synthesis of 1H-pyrazole-5-amines utilizing 1 M HCl at 150 °C was developed in order to provide products in a matter of minutes with minimal purification. Most reactions are complete in only 10 min and can be isolated via a simple filtration without the need for further purification by column chromatography or recrystallization. This method tolerates a range of functional groups and can be performed on milligram to gram scales.
- Everson, Nikalet,Yniguez, Kenya,Loop, Lauren,Lazaro, Horacio,Belanger, Briana,Koch, Grant,Bach, Jordan,Manjunath, Aashrita,Schioldager, Ryan,Law, Jarvis,Grabenauer, Megan,Eagon, Scott
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supporting information
p. 72 - 74
(2018/11/30)
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- Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model
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Psoriasis is a chronic T-cell-mediated autoimmune disease, and FMS-like tyrosine kinase 3 (FLT3) has been considered as a potential molecular target for the treatment of psoriasis. In this investigation, structural optimization was performed on a lead compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (1), which showed a moderate inhibitory activity againt FLT3. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis led to the discovery of a number of potent FLT3 inhibitors. One of the most active compounds, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (18b), was then chosen for in-depth antipsoriasis studies because this compound displayed the highest potency in a preliminary antipsoriasis test. Compound 18b exhibited significant antipsoriatic effects in the K14-VEGF transgenic mouse model of psoriasis, and no recurrence was found 15 days later after the last administration. Detailed mechanisms of action of compound 18b were also investigated. Collectively, compound 18b could be a potential drug candidate for psoriasis treatment.
- Li, Guo-Bo,Ma, Shuang,Yang, Ling-Ling,Ji, Sen,Fang, Zhen,Zhang, Guo,Wang, Li-Jiao,Zhong, Jie-Min,Xiong, Yu,Wang, Jiang-Hong,Huang, Shen-Zhen,Li, Lin-Li,Xiang, Rong,Niu, Dawen,Chen, Ying-Chun,Yang, Sheng-Yong
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p. 8293 - 8305
(2016/10/03)
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- FUSED CYCLOALKYL-PYRIMIDINE COMPOUNDS AND USES THEREOF
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Fused cycloalkyl-pyrimidine compounds that are kinase inhibitors, such as multi-kinase inhibitors, are provided. The compounds may be used in a method of treating cancer. Pharmaceutical compositions containing a fused cycloalkyl-pyrimidine compound and a pharmaceutically acceptable carrier are also provided, as are kits containing a fused cycloalkyl- pyrimidine compound or salt thereof and instructions for use, e.g., in a method of treating cancer.
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Paragraph 0219
(2016/01/25)
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- Discovery and optimization of a highly efficacious class of 5-aryl-2-aminopyridines as FMS-like tyrosine kinase 3 (FLT3) inhibitors
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Based on a putative binding mode of quizartinib (AC220, 1), a potent FMS-like tyrosine kinase 3 (FLT3) inhibitor in Phase III clinical development, we have designed de novo a simpler aminopyridine-based hinge binding motif. Further optimization focusing on maximizing in vivo efficacy and minimizing CYP3A4 time-dependent inhibition resulted in a highly efficacious compound (6s) in tumor xenograft model for further preclinical development.
- Liu, Gang,Abraham, Sunny,Liu, Xing,Xu, Shimin,Rooks, Allison M.,Nepomuceno, Ron,Dao, Alan,Brigham, Daniel,Gitnick, Dana,Insko, Darren E.,Gardner, Michael F.,Zarrinkar, Patrick P.,Christopher, Ron,Belli, Barbara,Armstrong, Robert C.,Holladay, Mark W.
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p. 3436 - 3441
(2015/08/11)
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- Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides
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A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is
- Mamuye, Ashenafi Damtew,Castoldi, Laura,Azzena, Ugo,Holzer, Wolfgang,Pace, Vittorio
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supporting information
p. 1969 - 1973
(2015/03/05)
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- Pyrazolotriazines as inhibitors of nucleases
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The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.
- -
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Paragraph 0060; 0061; 0062; 0063; 0064; 0078-0083
(2016/01/12)
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- Discovery of mixed type thymidine phosphorylase inhibitors endowed with antiangiogenic properties: Synthesis, pharmacological evaluation and molecular docking study of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones. Part II
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In our drug discovery program, a series of 2-thioxo-pyrazolo[1,5-a][1,3,5] triazin-4-ones were designed, synthesized and evaluated for their TP inhibitory potential. All the synthesized analogues conferred a varying degree of TP inhibitory activity, comparable or better than positive control, 7-deazaxanthine (7-DX, 2) (IC50 value = 42.63 μM). A systematic approach to the lead optimization identified compounds 3c and 4a as the most promising TP inhibitors, exhibiting mixed mode of enzyme inhibition. Moreover, selected compounds demonstrated the ability to attenuate the expression of the angiogenic markers (viz. MMP-9 and VEGF) in MDA-MB-231 cells at sublethal concentrations. In addition, molecular docking studies revealed the plausible binding orientation of these inhibitors towards TP, which was in accordance with the experimental results. Taken as a whole, these compounds would constitute a new direction for the design of novel TP inhibitors with promising antiangiogenic properties.
- Bera, Hriday,Ojha, Probir Kumar,Tan, Bee Jen,Sun, Lingyi,Dolzhenko, Anton V.,Chui, Wai-Keung,Chiu, Gigi Ngar Chee
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p. 294 - 303
(2014/04/17)
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- SUBSTITUTED HETEROAROMATIC PYRAZOLE-CONTAINING CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted heteroaromatic pyrazole-containing carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 104
(2013/03/26)
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- Substituted Heteroaromatic Pyrazole-Containing Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
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Substituted heteroaromatic pyrazole-containing carboxamide and urea compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds and also to a method of using these compounds for treating and/or inhibiting pain and further diseases and/or disorders.
- -
-
Paragraph 0667
(2013/03/26)
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CYCLIC GROUP AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an N-cyclic group as vanilloid receptor ligands formula (S) to pharmaceutical compositions containing these compounds of the general formula (S) and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 46
(2013/05/23)
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN O-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (Q) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 67
(2013/05/23)
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH A CO-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
-
The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with a CO-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
- -
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Page/Page column 48
(2013/05/23)
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN SO2-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
-
The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with a S02-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
- -
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Page/Page column 48
(2013/05/23)
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
-
The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (R) bearing a phenyl moiety substituted with an N-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
- -
-
Page/Page column 56
(2013/05/23)
-
- Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors
-
The present invention relates to the pyrazoloquinazolinone and pyrroloquinazolinone derivatives of the general formula (I), as well as pharmaceutical compositions containing them, and their use in the treatment and/or prophylaxis of conditions associated with altered glutamatergic signalling and/or functions, and/or conditions which can be affected by alteration of glutamate level or signalling in mammals, in particular their use in the treatment and/or prophylaxis of acute and chronic neurological and/or psychiatric disorders.
- -
-
Paragraph 0261
(2014/01/07)
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- SUBSTITUTED PYRAZOLOQUINAZOLINONES AND PYRROLOQUINAZOLINONES AS ALLOSTERIC MODULATORS OF GROUP II METABOTROPIC GLUTAMATE RECEPTORS
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The present invention relates to the pyrazoloquinazolinone and pyrroloquinazolinone derivatives of the general formula (I), as well as pharmaceutical compositions containing them, and their use in the treatment and/or prophylaxis of conditions associated with altered glutamatergic signalling and/or functions, and/or conditions which can be affected by alteration of glutamate level or signalling in mammals, in particular their use in the treatment and/or prophylaxis of acute and chronic neurological and/or psychiatric disorders.
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Page/Page column 94; 97
(2014/01/07)
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- Substituted Cyclic Carboxamide and Urea Derivatives as Ligands of the Vanilloid Receptor
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Substituted cyclic carboxamide and urea compounds, a process for their preparation, pharmaceutical compositions containing these compounds, and the use of these compounds for the treatment and/or inhibition of pain and other conditions mediated by the vanilloid receptor 1.
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Page/Page column 28; 29
(2012/03/10)
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- Substituted Heteroaromatic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
-
Substituted heteroaromatic carboxamide and urea compounds corresponding to formula (i) processes for the preparation thereof, pharmaceutical compositions containing these compounds and also a method of using these compounds in pharmaceutical compositions for treating or inhibiting pain and other conditions mediated at least in part via the vanilloid receptor 1.
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Page/Page column 33
(2012/05/20)
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- SUBSTITUTED HETEROAROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
-
The invention relates to substituted heteroaromatic carboxamide and urea derivatives of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
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Page/Page column 73
(2012/05/31)
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- Substituted Bicyclic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
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Substituted bicyclic carboxamide and urea compounds corresponding to formula (I) processes for the preparation thereof, pharmaceutical compositions containing these compounds, and a method of using these compounds for the treatment and/or inhibition of pain and other conditions mediated at least in part via the vanilloid receptor 1.
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Page/Page column 29
(2012/05/20)
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- SUBSTITUTED BICYCLIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted bicyclic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
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Page/Page column 72
(2012/05/31)
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- Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate
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Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles in presence of manganese(III) acetate produced ethyl 4-cyano-2,3-dihydrofuran-3-carboxylates and 4-cyano-2,3-dihydrofuran-3- carboxamides in good yields. The radical cyclizations of conjugated amides gave 2,3-dihydrofurans in better yields than that of conjugated esters. Moreover, the reactions of thienyl substituted amides and esters with 3-oxopropanenitriles afforded 2,3-dihydrofurans more efficiently than phenyl substituted ones. ARKAT-USA, Inc.
- Yilmaz, E. Vildan Burgaz,Yilmaz, Mehmet,Oektemer, Atilla
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body text
p. 363 - 376
(2011/09/20)
-
- SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
-
The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).
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Page/Page column 95
(2010/11/18)
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- SUBSTITUTED PHENYLLUREAS AND PHENYLAMIDES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted phenylureas and phenylamides of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
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Page/Page column 78
(2010/11/18)
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- Identification of 4-aminopyrazolylpyrimidines as potent inhibitors of Trk kinases
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The design, synthesis and biological evaluation of a series of 4-aminopyrazolylpyrimidines as potent Trk kinase inhibitors is reported. High-throughput screening identified a promising hit in the 4- aminopyrazolylpyrimidine chemotype. Initial optimization of the series led to more potent Trk inhibitors. Further optimization using two strategies resulted in significant improvement of physical properties and led to the discovery of 10z (AZ-23), a potent, orally bioavailable Trk A/B inhibitor. The compound offers the potential to test the hypothesis that modulation of Trk activity will be of benefit in the treatment of cancer and other indications in vivo.
- Wang, Tao,Lamb, Michelle L.,Scott, David A.,Wang, Haixia,Block, Michael H.,Lyne, Paul D.,Lee, John W.,Davies, Audrey M.,Zhang, Hai-Jun,Zhu, Yanyi,Gu, Fei,Han, Yongxin,Wang, Bin,Mohr, Peter J.,Kaus, Robert J.,Josey, John A.,Hoffmann, Ethan,Thress, Ken,MacIntyre, Terry,Wang, Haiyun,Omer, Charles A.,Yu, Dingwei
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scheme or table
p. 4672 - 4684
(2009/07/25)
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- Process for preparing beta-keto nitriles and salts thereof
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A process for preparing β-keto nitrites or salts thereof is provided by reacting a nitrile with a carboxylic ester in the presence of an alkali metal alkoxide or alkaline earth metal alkoxide. Alcohol formed as a by-product is distilled off. The volume of alcohol distilled off is continually replaced by metering in an essentially equal volume of nitrile. The nitrile is provided in excess based on the carboxylic ester to be converted.
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Page/Page column 6
(2008/06/13)
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- QUINAZOLINE DERIVATIVES
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The invention concerns quinazoline derivatives of Formula (I) or a pharmaceutically-acceptable salt, solvate or pro-drug thereof, wherein each of X1, p, R1, q, R2, R3, R4, R5, Ring A, r and R6 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders or in the treatment of disease states associated with angiogenesis and/or vascular permeability.
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Page/Page column 120
(2008/06/13)
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- PROCESS FOR PRODUCING BETA-KETONITRILE COMPOUND
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A process comprising reacting an aliphatic carboxylic ester compound with acetonitrile in the presence of a metal alkoxide to yield a metal salt of a β-ketonitrile compound, subsequently transferring the salt to an aqueous medium, and neutralizing the solution to obtain the β-ketonitrile compound in a free state, wherein a water-immisible organic solvent and water are added to the reaction mixture containing the β-ketonitrile compound metal salt yielded to transfer the metal salt to the water, the resultant aqueous solution of the β-keto-nitrile compound metal salt is separated from the organic solvent by phase separation or another technique and then neutralized, and the resultant free β-ketonitrile compound is taken out by extraction with an organic solvent.
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Page/Page column 9
(2008/06/13)
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- Herbicidal 2-cyano-1,3-diones
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Herbicides derived from 2-cyano-1,3-diones have the formula: STR1 wherein R, R1, R2 R3, R4 and R5 are as defined in the description. The compounds are intended for use pre- and post-emergence as selective herbicides in maize and a large number of other monocotyledon crops.
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- Aryl halides as precursors of electrogenerated bases. Utilization in coupling reactions of acetonitrile with various electrophilic compounds
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An electrochemical alternative to classical cyanomethylation is possible by using electrogenerated bases (EGBs), obtained by electroreduction of aryl halides in an undivided cell fitted with a cadmium coated cathode and a sacrificial magnesium anode. Acetonitrile is used both as solvent and as hydrogen-active compound. A coupling reaction with various electrophilic compounds was carried out. When the electrophilic compound was present from the beginning of the electrolysis, the expected coupling product with the cyanomethyl anion was obtained. If the electrophilic compound was added only after complete electrolysis of the aryl halide, dimerization of the cyanomethyl anion and a coupling reaction between the dimer anion and the electrophilic compound were observed.
- Barhdadi, Rachid,Gal, Jacques,Heintz, Monique,Troupel, Michel,Perichon, Jacques
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p. 5091 - 5098
(2007/10/02)
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- Inhibitors of the advanced glycosylation of proteins and methods of use therefor
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The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of an early glycosylation product of such target proteins resulting from their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
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- Aryl Halides as Convenient Precursors of Electrogenerated Bases. Efficient Syntheses of β-Oxo Nitriles or Esters by Coupling Active-hydrogen Groups with Esters
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In an undivided cell fitted with a sacrificial anode and a nickel cathode on which cadmium had been deposited, the electroreduction of aromatic halides affords a strong base which allows the effective synthesis of β-oxo nitriles or β-oxo esters from the coupling of active-hydrogen compounds with esters.
- Barhdadi, Rachid,Gal, Jacques,Heintz, Monique,Troupel, Michel
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- The Syntheses of 5-Amino-3-t-butylisothiazole and 3-Amino-5-t-butylisothiazole
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A general synthesis of 3-amino-3-alkylpropenenitriles is described.These intermediates are further transformed to 5-amino-3-alkylisothiazoles.Also described is the synthesis of the novel isomer, 3-amino-5-t-butylisothiazole.
- Hackler, Ronald E.,Burow, Kenneth W.,Kaster, Sylvester V.,Wickiser, David I.
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p. 1575 - 1578
(2007/10/02)
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- Herbicidally active enols
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Enols, their geometric isomers, tautomers and halogen addition products having the formula STR1 as defined herein and compositions containing these compounds exhibit herbicidal activity.
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- Process for the production of 3-oxonitriles
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3-oxonitriles are produced by reaction of carboxylic acid esters with carboxylic acid nitriles in the presence of 70 to 80% suspension of sodium hydride in white oil. The oxonitrile are intermediate products for the production of 3-oxocarboxylic acid amides or esters and pesticides.
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- Benzamides, compositions and agricultural method
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N-Aryl benzamides wherein the aryl group is a nitrogen containing heterocycle are useful as selective herbicidal agents. Compositions containing the novel benzamides and a herbicidal method of selective weed control are disclosed.
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- Process for the production of cyanopinacolone
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Cyanopinacolone is produced by reacting pinacolone with about 1.0 to about 1.2 molar equivalents of chlorine in methanol and further reacting the resulting monochloropinacolone with about 1.0 to about 1.2 molar equivalents of an alkali metal cyanide in methanol.
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