Ethanamine, 2,2,2-trifluoro- → 6-[3-(4-Fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-N-(2,2,2-trifluoro-ethyl)-nicotinamide

HRID 83265Notes

Reaction equation

HRID 83265 reaction equation
CO[C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:14][O:15][C:16]=2[C:17]([F:20])([F:19])[F:18])=[N:6][CH:5]=1.COC(=O)C1C=CC(OCC2C(C3C=CC=C(F)C=3)=NOC=2C)=NC=1.[F:54][C:55]([F:59])([F:58])[CH2:56][NH2:57]>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([NH:57][CH2:56][C:55]([F:59])([F:58])[F:54])=[O:28])=[CH:5][N:6]=3)=[C:16]([C:17]([F:18])([F:19])[F:20])[O:15][N:14]=2)=[CH:22][CH:23]=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 684447756-[3-(4-Fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 866309096-[3-(4-Fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-N-(2,2,2-trifluoro-ethyl)-nicotinamideYield 98%

Procedure

As described for example 92, 6-[3-(4-fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.25 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 (115 mg, 98%) which was obtained as a white solid. MS: m/e=464.3 [M+H]+.

Sources & evidence

ORD record
ord-067c7153d2554c52bb80336ead376f12
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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