Ethanamine, 2,2,2-trifluoro- → 5-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 1695348Notes

Reaction equation

HRID 1695348 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][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].COC(C1NN=C(OCC2C(C3C=CC=CC=3)=NOC=2C)C=1)=O.[F:48][C:49]([F:53])([F:52])[CH2:50][NH2:51]>>[F:48][C:49]([F:53])([F:52])[CH2:50][NH:51][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][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4]

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 666438035-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl esterHCID 66643884HCID 66643884, compound

Product 1

HCID 497929195-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid (2,2,2-trifluoro-ethyl)-amideYield 21%

Procedure

As described for example 1b, 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.3 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using 2,2,2-trifluoroethylamine instead of morpholine, to the title compound (25 mg, 21%), which was obtained as a white solid. MS: m/e=400.0 [M+H]+.

Sources & evidence

ORD record
ord-58244a11d667434b96561f21aefc8ee3
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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