5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid → 5-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamide

HRID 1695374Notes

Reaction equation

HRID 1695374 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([C:17]([OH:19])=O)[NH:15][N:16]=2)=[C:8]([CH3:20])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].FC1C=CC(C2C(CO[C:35]3[CH:36]=[C:37]([C:40](O)=O)[NH:38][N:39]=3)=C(C)ON=2)=CC=1>>[N:39]1([NH:38][C:17]([C:14]2[NH:15][N:16]=[C:12]([O:11][CH2:10][C:9]3[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=3[CH3:20])[CH:13]=2)=[O:19])[CH2:40][CH2:37][CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 666436795-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acidHCID 666438195-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid

Product 1

HCID 595684535-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamideYield 48%

Procedure

As described for example 10b, 5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid (140 mg, 0.5 mmol), instead of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid, was converted, to the title compound (83 mg, 48%), which was obtained as a white solid. MS: m/e=348.3 [M+H]+.

Sources & evidence

ORD record
ord-e1625ccd78ef4eebbd3c5a3b70db7d87
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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