Ethanamine, 2,2,2-trifluoro- → 6-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-nicotinamide

HRID 83388Notes

Reaction equation

HRID 83388 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[F:25][C:26]([F:30])([F:29])[CH2:27][NH2:28]>>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:28][CH2:27][C:26]([F:30])([F:29])[F:25])=[O:24])=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 684445186-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 426301686-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-nicotinamideYield 98%

Procedure

As described for example 272, 6-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (97.6 mg, 0.3 mmol) was converted, using 2,2,2-trifluoroethylamine instead of 4-aminotetrahydropyran, to the title compound (115 mg, 98%) which was obtained as a white solid. MS: m/e=393.4 [M+H]+.

Sources & evidence

ORD record
ord-1545b614b5bd4e5eb0c78815cdc21e52
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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