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

HRID 930034Notes

Reaction equation

HRID 930034 reaction equation
[Li].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:15]([O-])=[CH:16][C:17](=O)[C:18]([O:20]CC)=[O:19])[CH:7]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:9]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:48][C:49]1[CH:54]=[C:53]([NH:55][NH2:56])[CH:52]=[CH:51][N:50]=1>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:15]2[N:55]([C:53]3[CH:52]=[CH:51][N:50]=[C:49]([Cl:48])[CH:54]=3)[N:56]=[C:17]([C:18]([OH:20])=[O:19])[CH:16]=2)[CH:7]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:9]=1

Participants

4

Reactant 3

HCID 865938392-Chloro-4-hydrazinylpyridine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735136Lithium 1-(3-methoxy-5-trifluoromethoxyphenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896028375-(3-Methoxy-5-trifluoromethoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

500 mg (1.29 mmol) of the compound of Example 10A is reacted analogously to the synthesis of the compound of Example 20A with 256 mg (1.42 mmol) of 2-chloropyridin-4-yl-hydrazine hydrochloride. After hydrolysis, 149 mg (28% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-df32efde80f3458ab37210f2ee7857d4
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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