2-Chloro-4-hydrazinylpyridine hydrochloride → 5-(3-Fluoro-5-difluoromethoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930030Notes

Reaction equation

HRID 930030 reaction equation
[Li].[F:2][CH:3]([F:22])[O:4][C:5]1[CH:6]=[C:7]([C:12]([O-])=[CH:13][C:14](=O)[C:15]([O:17]CC)=[O:16])[CH:8]=[C:9]([F:11])[CH:10]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:46][C:47]1[CH:52]=[C:51]([NH:53][NH2:54])[CH:50]=[CH:49][N:48]=1>>[F:11][C:9]1[CH:8]=[C:7]([C:12]2[N:53]([C:51]3[CH:50]=[CH:49][N:48]=[C:47]([Cl:46])[CH:52]=3)[N:54]=[C:14]([C:15]([OH:17])=[O:16])[CH:13]=2)[CH:6]=[C:5]([O:4][CH:3]([F:2])[F:22])[CH:10]=1

Participants

4

Reactant 3

HCID 865938392-Chloro-4-hydrazinylpyridine hydrochlorideHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131735133Lithium 1-(3-difluoromethoxy-5-fluorophenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896099575-(3-Fluoro-5-difluoromethoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

590 mg (1.01 mmol) of the compound of Example 7A is reacted analogously to the synthesis of the compound of Example 20A with 200 mg (1.11 mmol) of 2-chloropyridin-4-yl-hydrazine hydrochloride. After hydrolysis, 160 mg (41% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-9da9ee2b2ba0474794d3af94ada02e9b
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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