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

HRID 1521140Notes

Reaction equation

HRID 1521140 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:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.COC(=O)C1C=CC(OCC2C(C3C=CC=C(F)C=3)=NOC=2C)=NC=1.[F:50][C:51]([F:55])([F:54])[CH2:52][NH2:53]>>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:53][CH2:52][C:51]([F:55])([F:54])[F:50])=[O:24])=[CH:5][N:6]=1

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 684418946-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl esterHCID 68442066HCID 68442066, compound

Product 1

HCID 684453316-(5-Methyl-3-pyridin-3-yl-isoxazol-4-ylmethoxy)-N-(2,2,2-trifluoro-ethyl)-nicotinamideYield 89%

Procedure

As described for example 92, 6-(5-methyl-3-pyridin-3-yl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (130 mg, 0.4 mmol), instead of 6-[3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester, was converted, using 2,2,2-trifluoroethylamine instead of cyclopropylamine, to the title compound (139 mg, 89%) which was obtained as an off white solid. MS: m/e=393.1 [M+H]+.

Sources & evidence

ORD record
ord-75b6ab0ea7be4fb1864a12f9e4afa875
Source dataset
uspto-grants-2015_07
Patent number
US09073908B2

Reaction notes

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