- Synthesis process 2 - methyl -3 - methoxybenzoic acid
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The invention discloses a synthesis process of 2 - methyl -3 - methoxybenzoic acid, which comprises the following steps: (1) reducing hydrogenation reaction: taking 2 - methyl -3 - nitrobenzoic acid or 2 - methyl -3 - nitrobenzoate as raw materials and methanol as a solvent. The hydrogen is a hydrogen source, and palladium carbon or platinum carbon is used as a catalyst to prepare 3 - amino -2 - methyl benzoic acid or 3 - amino -2 - methyl benzoic acid methyl ester by hydrogenation reduction. (2) Diazotization and hydrolysis and esterification one-pot reaction: preparing and hydroxyl 3 - methyl benzoic acid methyl ester by carrying out diazotization and hydrolysis -2 - esterification reaction under the action of a reducing product as a raw material and methanol as a solvent and a diazotization reagent. (3) Methylation reaction: methyl benzoate serving 3 - hydroxyl -2 - is used as a raw material, dimethyl sulfate is used as a methylation reagent, and methyl benzoate is produced 3 - methoxy -2 - methyl benzoate in the presence of a base. (4) Hydrolysis Reaction: methyl 3 - methoxy -2 - methyl benzoate and base. Water is mixed, heated and hydrolyzed, the reaction is complete, the product precipitated by acid conditioning PH through 1-3, filtered, and dried to obtain 3 - methoxy -2 -methylbenzoic acid.
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Paragraph 0053-0054
(2021/10/20)
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- Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air
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L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.
- Bao, Xuefei,Chen, Guoliang,Dong, Jinhua,Du, Fangyu,Li, Hui,Liang, Xinjie,Wu, Ying,Zhang, Yongsheng
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supporting information
(2020/08/03)
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- Application of quebrachitol in hydrolysis reaction of copper-catalyzed aryl halide
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The invention belongs to the technical field of drug synthesis, and provides application of quebrachitol in a hydrolysis reaction of a copper-catalyzed aryl halide. According to the hydrolysis reaction, copper serves as a catalyst, quebrachitol serves as a ligand, and the hydrolysis reaction is carried out on the aryl halide. The invention further provides a catalytic system of the hydrolysis reaction of the aryl halide. The reaction system comprises the copper catalyst, the quebrachitol, alkali and water, and the system is environmentally friendly and is suitable for industrial application.
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Paragraph 0081-0083
(2019/07/16)
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- Aryl carboxylic acid and aryl tetrazole derivatives as IP receptor modulators
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This invention relates to compounds which are generally IP receptor modulators, particularly IP receptor agonists, and which are represented by Formula I: wherein R1, R2, R3, R4, R5, A, and B are as defined in the specification, and individual isomers, racemic or non-racemic mixtures of isomers, and pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds and methods for their use as therapeutic agents.
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Page column 29
(2010/02/04)
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- Process for making 2-alkyl-3-hydroxybenzoic acids
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A two step process is described for making 2-alkyl-3-hydroxybenzoic acids or derivatives of benzoic acids by first reacting an allenyl ester or equivalent with furan followed by the ring-opening reaction of the derived bicyclo intermediate with base. The
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- Process for synthesizing benzoic acids
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A nucleophilic substitution reaction on optionally substituted dihalobenzenes is carried out in the presence of an optional catalyst followed by formation of and subsequent carboxylation of a Grignard reaction intermediate. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids from 1-substituted 2,6-dihalobenzenes. The invention also provides a process for the direct formation of an acyl chloride from a Grignard reagent by quenching with phosgene.
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- Benzodioxincarboxylic acid hydrazides as insecticides
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The present invention is concerned with benzodioxincarboxylic acids and esters, N'-substituted N,N'-diacylhydrazines prepared from benzodioxincarboxylic acids and esters, insecticidal compositions containing the N'-substituted N,N'-diacylhydrazines, and t
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- Bicyclic inhibitors of protein farnesyl transferase
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PCT No. PCT/US98/03025 Sec. 371 Date Aug. 2, 1999 Sec. 102(e) Date Aug. 2, 1999 PCT Filed Feb. 11, 1998 PCT Pub. No. WO98/34921 PCT Pub. Date Aug. 13, 1998The present invention provides compounds of Formula (I). The present invention also provides a metho
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- Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
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PCT No. PCT/US94/09139 Sec. 371 Date Jan. 24, 1996 Sec. 102(e) Date Jan. 24, 1996 PCT Filed Aug. 23, 1994 PCT Pub. No. WO95/06030 PCT Pub. Date Mar. 2, 1995The invention relates to sulfonamide-containing hydroxyethylamine protease inhibitor compounds, their process of making, composition and method of use for inhibiting retroviral proteases such as human immunodeficiency virus.
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- Bis-sulfonamide hydroxyethylamino retroviral protease inhibitors
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PCT No. PCT/US96/00607 Sec. 371 Date Feb. 26, 1998 Sec. 102(e) Date Feb. 26, 1998 PCT Filed Jan. 18, 1996 PCT Pub. No. WO96/22287 PCT Pub. Date Jul. 25, 1996Bis-sulfonamido hydroxyethylamino compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to retroviral protease inhibiting compounds of the formula: or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein the variables are as defined herein.
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- Process for making 2-alkyl-3-hydroxybenzoic acids
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A two step process is described for making 2-alkyl-3-hydroxybenzoic acids or derivatives of benzoic acids by first reacting an allenyl ester or equivalent with furan followed by the ring-opening reaction of the derived bicyclo intermediate with base. The
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- Synthesis of isothiochroman 2,2-dioxide and 1,2-benzooxathiin 2,2- dioxide gyrase B inhibitors
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The design, synthesis and in vitro biological evaluation of isothiochroman 2,2-dioxide and 1,2-benzooxathiin 2,2-dioxide analogues of coumarin inhibitors of gyrase B are described. Compared to coumarin derivatives, compounds of the 1,2-benzooxathiin 2,2-dioxide series display improved inhibitory potency in negative supercoiling of relaxed DNA gyrase. (C) 2000 Elsevier Science Ltd.
- Peixoto, Christophe,Laurin, Patrick,Klich, Michel,Dupuis-Hamelin, Claudine,Mauvais, Pascale,Lassaigne, Patrice,Bonnefoy, Alain,Musicki, Branislav
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p. 1741 - 1745
(2007/10/03)
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- Relationships between structure and molting hormonal activity of tebufenozide, methoxyfenozide, and their analogs in cultured integument system of Chilo suppressalis Walker
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The molting hormonal activity of methoxyfenozide (RH-2485), tebufenozide (RH-5992), five analogs with various alkyl groups, and 18 acyl analogs was measured by using cultured integument of rice stem borers, Chilo suppressalis Walker. The hormonal activity of methoxyfenozide was remarkably high (EC50 = 1.1 x 10-9 M), being equivalent to that of tebufenozide (RH-5992). The hormonal activity of several tebufenozide analogs with varying alkyl groups such as CH3, n-C3H7, i-C3H7, n-C4H9 and n-C5H11 at the para-position of the benzene ring furthest from the tert-butyl group was lower than that of tebufenozide (alkyl group is C2H5). The activity decreased to varying degrees as a result of replacement of the 3,5-dimethylphenyl moiety of tebufenozide with either a phenyl, naphthyl, or cyclohexyl group. Both 1- and 2-naphthyl derivatives were very active (EC50 = 4.3 x 10-8 M and 3.2 x 10-8 M, respectively) without any significant difference between them. The activity of the 1-cyclohexenyl analog (EC50 = 1.0 x 10-7 M) was about 40x that of the corresponding 3-cyclohexenyl analog (EC50 = 4.4 x 10-6 M), but 1/100 that of tebufenozide. The activity varied parabolically with respect to the molecular hydrophobicity, and decreased with longer acyl moieties. Copyright (C) 2000 Elsevier Science Inc.
- Nakagawa, Yoshiaki,Hattori, Kazunari,Minakuchi, Chieka,Kugimiya, Soichi,Ueno, Tamio
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p. 117 - 123
(2007/10/03)
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- HIV protease inhibitors
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HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.
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- Process for synthesizing benzoic acids
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Nucleophilic substitution reactions on halobenzenes or triflyl substituted benzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes, 2-halo-6-triflylbenzene and 2,6-ditriflylbenzenes.
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- Viracept (nelfinavir mesylate, AG1343): A potent, orally bioavailable inhibitor of HIV-1 protease
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Using a combination of iterative structure-based design and an analysis of oral pharmacokinetics and antiviral activity, AG1343 (Viracept, nelfinavir mesylate), a nonpeptidic inhibitor of HIV-1 protease, was identified. AG1343 is a potent enzyme inhibitor
- Kaldor, Stephen W.,Kalish, Vincent J.,Davies II, Jay F.,Shetty, Bhasker V.,Fritz, James E.,Appelt, Krzysztof,Burgess, Jeffrey A.,Campanale, Kristina M.,Chirgadze, Nickolay Y.,Clawson, David K.,Dressman, Bruce A.,Hatch, Steven D.,Khalil, Deborah A.,Kosa, Maha B.,Lubbehusen, Penny P.,Muesing, Mark A.,Patick, Amy K.,Reich, Siegfried H.,Su, Kenneth S.,Tatlock, John H.
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p. 3979 - 3985
(2007/10/03)
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- HIV protease inhibitors
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HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.
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- (Hydroxyethyl) sulfonamide HIV-1 protease inhibitors: Identification of the 2-methylbenzoyl moiety at P-2
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We have discovered a potent low molecular weight series of HIV-1 protease inhibitors incorporating the (R)-(hydroxyethyl) sulfonamide isostere.
- Freskos,Bertenshaw,Getman,Heintz,Mischke,Blystone,Bryant,Funckes-Shippy,Houseman,Kishore,Kocan,Mehta
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p. 445 - 450
(2007/10/03)
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- HIV protease inhibitors
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HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain the
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- Intermediate and process for making
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The present invention provides novel HIV protease inhibitors, pharmaceutical formulations containing those compounds and methods of treating and/or preventing HIV infection and/or AIDS.
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- Trisubstituted benzoic acid intermediates
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2-methyl-3-(substituted)-4-(substituted) benzoic acids or their alkyl ester that are useful to prepare herbicidal compounds.
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- REVISION OF THE STRUCTURE ASSIGNED TO A MONOTERPENE ISOLATED FROM PIQUERIA TRINERVIA
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Unambiguous synthesis of 2-methyl-3-isopropenylanisole (1) and 2-isopropenyl-3-methylanisole (4) has led to revision, from (1) to (4), of the structure assigned to a monoterpene phenol ether isolated from Piqueria trinervia.
- Sangaiah, R.,Rao, G. S. Krishna
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p. 1843 - 1844
(2007/10/02)
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