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

HRID 1695387Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:6]([CH3:25])[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.COC(C1NN=C(OCC2C(C3C=CC=CC=3)=NOC=2C)C=1)=O.[CH3:49][N:50]([CH3:52])[NH2:51]>>[CH3:49][N:50]([CH3:52])[NH:51][C:3]([C:5]1[N:6]([CH3:25])[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:2]

Participants

Reactant 3

HCID 59761,1-Dimethylhydrazine

HCID 66643823HCID 66643823, compound

HCID 66643884HCID 66643884, compound

Product 1

HCID 595684475-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid N',N'-dimethyl-hydrazideYield 96%

Procedure

As described for example 1b, 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (110 mg, 0.32 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using N,N-dimethylhydrazine instead of morpholine, to the title compound (114 mg, 96%) which was obtained as a white foam. MS: m/e=374.2 [M+H]+.

Sources & evidence

ORD record: ord-5778a3898a654038b9089d829ab0c1c3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

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