1,1-Dimethylhydrazine → 5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid N',N'-dimethyl-hydrazide

HRID 1695339Notes

Reaction equation

HRID 1695339 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].[CH3:25][N:26]([CH3:28])[NH2:27]>>[CH3:25][N:26]([CH3:28])[NH:27][C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 666438345-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 497928975-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid N',N'-dimethyl-hydrazideYield 23%

Procedure

As described for example 8b, 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.3 mmol) was converted, using N,N-dimethylhydrazine instead of 4-aminomorpholine, to the title compound (25 mg, 23%), which was obtained as a white solid after recrystallization from ethyl acetate. MS: m/e=360.2 [M+H]+.

Sources & evidence

ORD record
ord-62f47c2a8722474693fc986369ad4d00
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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