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

HRID 1695356Notes

Reaction equation

HRID 1695356 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:20]([OH:22])=O)[NH:18][N:19]=3)=[C:11]([CH3:23])[O:10][N:9]=2)=[N:6][CH:7]=1.FC1C=CC(C2C(CO[C:38]3[CH:39]=[C:40]([C:43](O)=O)[NH:41][N:42]=3)=C(C)ON=2)=CC=1>>[N:42]1([NH:41][C:20]([C:17]2[NH:18][N:19]=[C:15]([O:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=4)=[N:9][O:10][C:11]=3[CH3:23])[CH:16]=2)=[O:22])[CH2:43][CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 666436795-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acidHCID 666438905-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid

Product 1

HCID 595684755-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamideYield 39%

Procedure

As described for example 10b, 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid (38 mg, 0.12 mmol), instead of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid, was converted, to the title compound (18 mg, 39%) which was obtained as a white solid. MS: m/e=387.2 [M+H]+.

Sources & evidence

ORD record
ord-a645697f81174f8aae0e149a3f143664
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

Loading…