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

HRID 930029Notes

Reaction equation

HRID 930029 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.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([NH:52][NH2:53])[CH:47]=1>>[F:11][C:9]1[CH:8]=[C:7]([C:12]2[N:52]([C:48]3[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=3)[N:53]=[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 231434543-Hydrazinylpyridine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735133Lithium 1-(3-difluoromethoxy-5-fluorophenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

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 of Example 7A is reacted analogously to the synthesis of the compound of Example 20A with 161 mg (1.11 mmol) of 3-pyridylhydrazine hydrochloride. After hydrolysis, 150 mg (43% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-317e9689e9644cf4a5647b5f5c28f2b3
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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