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

HRID 930031Notes

Reaction equation

HRID 930031 reaction equation
[Li].[Cl:2][C:3]1[CH:4]=[C:5]([C:13]([O-])=[CH:14][C:15](=O)[C:16]([O:18]CC)=[O:17])[CH:6]=[C:7]([O:9][CH:10]([F:12])[F:11])[CH:8]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([NH:52][NH2:53])[CH:47]=1>>[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[N:52]([C:48]3[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=3)[N:53]=[C:15]([C:16]([OH:18])=[O:17])[CH:14]=2)[CH:6]=[C:7]([O:9][CH:10]([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 3

HCID 231434543-Hydrazinylpyridine hydrochlorideHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131735134Lithium 1-(3-chloro-5-difluoromethoxyphenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896024835-(3-Chloro-5-difluoromethoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

350 mg (0.80 mmol) of the compound of Example 8A is reacted analogously to the synthesis of the compound of Example 20A with 128 mg (0.88 mmol) of 3-pyridylhydrazine hydrochloride. After hydrolysis, 176 mg (60% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-8426fb449f674cedb2ca8b3a82130716
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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