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

HRID 930013Notes

Reaction equation

HRID 930013 reaction equation
[Li].[Cl:2][C:3]1[CH:4]=[C:5]([C:14]([O-])=[CH:15][C:16](=O)[C:17]([O:19]CC)=[O:18])[CH:6]=[C:7]([O:9][C:10]([F:13])([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:47]1[CH:52]=[CH:51][CH:50]=[C:49]([NH:53][NH2:54])[CH:48]=1>>[Cl:2][C:3]1[CH:4]=[C:5]([C:14]2[N:53]([C:49]3[CH:48]=[N:47][CH:52]=[CH:51][CH:50]=3)[N:54]=[C:16]([C:17]([OH:19])=[O:18])[CH:15]=2)[CH:6]=[C:7]([O:9][C:10]([F:11])([F:12])[F:13])[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 131735131Lithium 1-(3-chloro-5-trifluoromethoxyphenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896024635-(3-Chloro-5-trifluoromethoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

500 mg (1.23 mmol) of the compound of Example 4A is reacted analogously to the synthesis of the compound of Example 20A with 197 mg (1.36 mmol) of 3-pyridylhydrazine hydrochloride. After hydrolysis, 203 mg (43% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-6f2ba4f38e9d4f45878c2b80a13bf10d
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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