3-Hydrazinylpyridine hydrochloride → 5-(3-Fluoro-5-difluoromethoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 1771910Notes

Reaction equation

HRID 1771910 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.ClC1C=C(N2[C:22]([C:23]3[CH:28]=[C:27]([O:29][C:30](F)([F:32])[F:31])[CH:26]=[C:25]([F:34])[CH:24]=3)=[CH:21][C:20]([C:35]([OH:37])=[O:36])=N2)C=CC=1F>>[F:34][C:25]1[CH:24]=[C:23]([C:22]2[N:8]([C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)[N:9]=[C:20]([C:35]([OH:37])=[O:36])[CH:21]=2)[CH:28]=[C:27]([O:29][CH:30]([F:32])[F:31])[CH:26]=1

Participants

3

Reactant 2

HCID 231434543-Hydrazinylpyridine hydrochlorideHCID 582772891-(3-chloro-4-fluorophenyl)-5-(3-fluoro-5-trifluoromethoxyphenyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 896025115-(3-Fluoro-5-difluoromethoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

590 mg (1.01 mmol) of the compound from example 4A is reacted with 161 mg (1.11 mmol) 3-pyridylhydrazine hydrochloride in a manner analogous to the synthesis of the compound from example 8A. Following hydrolysis, 150 mg (43% of theoretical yield) of the title compound is produced.

Sources & evidence

ORD record
ord-9b5e7009b8e44b16874ddb7f94a3ecbc
Source dataset
uspto-grants-2016_02
Patent number
US09249148B2

Reaction notes

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