5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 7-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amide

HRID 564743Notes

Reaction equation

HRID 564743 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[C:14]3[CH:25]=[C:24]([CH2:26][CH3:27])[O:23][C:15]=3[C:16]([O:19][CH:20]([F:22])[F:21])=[N:17][CH:18]=2)=[O:12])=CC=1)([O-])=O.[NH2:28][C:29]1[N:33]([CH3:34])[N:32]=[CH:31][C:30]=1[C:35]#[N:36]>>[C:35]([C:30]1[CH:31]=[N:32][N:33]([CH3:34])[C:29]=1[NH:28][C:11]([C:13]1[C:14]2[CH:25]=[C:24]([CH2:26][CH3:27])[O:23][C:15]=2[C:16]([O:19][CH:20]([F:21])[F:22])=[N:17][CH:18]=1)=[O:12])#[N:36]

Participants

3

Reactant 2

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 538910297-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 572556447-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amideYield 52.3%

Procedure

Starting from 7-difluromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (100 mg) and 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (65 mg). Purification by column chromatography on silica eluting with 2-3% methanol in dichloromethane followed by trituration with diethyl ether afforded the title compound as a white solid (50 mg).

Workup

  1. customPurification by column chromatography on silica eluting with 2-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-2eebb217b8e74b758cef328777acefe5
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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