- Synthesis method of garafloxacin intermediate
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The invention discloses a synthesis method of a garafloxacin intermediate (1R)-5-bromo-2, 3-dihydro-1-methyl-1H-isoindole; the synthesis method comprises the following steps of: taking a garafloxacin intermediate as a raw material; the method comprises the following steps: step 1, by taking R(+)-alpha-phenylethylamine as a raw material and lewis acid as a catalyst, carrying out bromine bromination reaction to obtain a compound 2; 2, placing the compound 2 in a solvent, adding hydrochloric acid, paraformaldehyde and a catalyst, and carrying out chloromethylation reaction to obtain a compound 3; 3, dissolving the compound 3 in a solvent, adding alkali, and heating the mixture for reaction to obtain a compound 1. The method is simple in reaction, short in route, less in three wastes, environment-friendly, high in yield of each step, less in waste of raw materials and reagents, and especially suitable for industrial production.
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- Preparation method of (1R)-5-bromo-2,3-dihydro-1-methyl-1H-isoindole
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The invention discloses a preparation method of (1R)-5-bromo-2,3-dihydro-1-methyl-1H-isoindole. The preparation method comprises the following steps: dissolving 3-bromobenzaldehyde in a first solvent,adding ammonia water and a catalyst, carrying out a reaction in a hydrogen atmosphere, and then performing filtering and concentrating to obtain a first reaction product; dissolving the first reaction product in a second solvent, carrying out cooling to -20 to 20 DEG C, dropwise adding an inorganic acid, adding an aqueous acetaldehyde solution, carrying out heating to a reflux temperature, carrying out a reaction for 5 to 15 h, carrying out reduced-pressure concentration until a volume is 1/3 of an original volume, adjusting a pH value to 9 to 10, conducting stirring overnight, and carrying out suction filtration and recrystallization to obtain a second reaction product; dissolving the second reaction product in a third solvent, dropwise adding a resolving agent, keeping the formed solution at a temperature at 40-80 DEG C for 1-7 hours, performing reduced-pressure concentration until the volume of the solution is reduced by 1/2, conducting stirring overnight at room temperature, and performing suction filtration and washing; and adding the obtained solid into water, slightly heating the solid to dissolve the solid, adjusting a pH value to 9-10, cooling the formed solution to 10 DEG C, carrying out stirring overnight, and performing suction filtration to obtain a target product. The preparation method has the advantages of simple operation, usage of easily available raw materials, reduced cost and applicability to industrial production.
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Paragraph 0050; 0052; 0054; 0056; 0058; 0060; 0062; 0064
(2020/04/17)
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- Traceless Directing Group Assisted Cobalt-Catalyzed C?H Carbonylation of Benzylamines
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The first example of cobalt-catalyzed C(sp2)?H carbonylation of benzylamines using a traceless directing group is reported, which was successfully applied to the synthesis of N?unprotected iso-indolinones through direct C?H/N?H bonds activation. This protocol tolerates a variety of functional groups and provides a facile and efficient method for the formal synthesis of (+)-garenoxacin. (Figure presented.).
- Ling, Fei,Ai, Chongren,Lv, Yaping,Zhong, Weihui
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supporting information
p. 3707 - 3712
(2017/10/07)
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- A (R)- N - Boc - 5 - bromo - 1 - methyl isobutyl ketone indoline and its preparation method and application (by machine translation)
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The present invention provides a kind of (R)- N - Boc - 5 - bromo - 1 - methyl isobutyl ketone indoline and its preparation method and application, (R)- 4 - bromo - α - phenethylamine in under the action of Lewis acid poly formaldehyde reaction, to obtain the (R)- 5 - bromo - 1 - methyl isobutyl ketone indoline, and then using the tert-butoxy carbonyl amino can be obtained by protecting the (R)- N - Boc - 5 - bromo - 1 - methyl isobutyl ketone indoline, the ring method step is novel and unique, easy operation, the yield is higher. The use of split reagent first split to get chiral raw materials for preparing (R)- 4 - bromo - α - phenethylamine, and then prepare to obtain (R)- 5 - bromo - 1 - methyl isobutyl ketone indoline, makes it possible to greatly reduce the quantity, the quantity is greatly reduced, the whole process of splitting of waste is greatly reduced. The whole of this invention the method of preparing the raw materials are easy, simple process operation, low cost, and has relatively high practical application value. (by machine translation)
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Paragraph 0062-0064; 0076-0078; 0090-0092
(2017/08/31)
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- NOVEL COMPOUND WITH ANTIBACTERIAL ACTIVITY
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A compound represented by the general formula (I) or a salt thereof having a potent antibacterial activity against bacteria that have acquired resistance to quinolones, and a medicament for prophylactic and/or therapeutic treatment of an infectious disease containing the compound or a salt thereof as an active ingredient, as well as a medicament for prophylactic and/or therapeutic treatment of an infectious disease containing a combination of the compound or a salt thereof, and a quinolone.
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- CYCLOALKYL NITRILE PYRAZOLO PYRIDONES AS JANUS KINASE INHIBITORS
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Compounds of formula I are provided, which are JAK inhibitors and are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.
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Page/Page column 145; 146
(2014/10/03)
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- Processes for producing 7-isoindolinequinolonecarboxylic derivatives and intermediates therefor, salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and composition containing the same as active ingredient
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This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1represents a hydrogen atom or a carboxyl-protecting group; R2represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted amino groups, alkylidene groups, oxo group and groups each forming a cycloalkane group together with the carbon atom to which R4bonds; R5represents a hydrogen atom, an amino-protecting group, a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R6represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group or a nitro group; and A represents CH or C—R7in which R7represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group or a protected or unprotected hydroxyl group, and to a salt of a 7-isoindoline-quinolonecarboxylic acid represented by the general formula [1], a hydrate thereof and a composition comprising them as an active ingredient.
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Example II-7
(2010/11/29)
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- 4-Oxoquinolizine antimicrobial having 2-pyridone skeleton as partial structure
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A compound represented by the following Formula (I) or a pharmaceutically acceptable salt thereof: 1wherein R1 represents a hydrogen atom or a carboxyl-protecting group, R2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a hydroxyl group, R3 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a nitro group, a cyano group, a hydroxyl group or an amino group; R4 represents a hydrogen atom, an amino-protecting group, an alkyl group or a cycloalkyl group, and R5 represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an alkylthio group, a hydroxyl group, an imino group or an amino group.
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