Ethanamine, 2,2,2-trifluoro- → 5-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 1962991Notes

Reaction equation

HRID 1962991 reaction equation
C(O[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[CH:8][N:7]=1)=[O:5])C.[F:28][C:29]([F:33])([F:32])[CH2:30][NH2:31]>>[F:28][C:29]([F:33])([F:32])[CH2:30][NH:31][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[CH:8][N:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 666445155-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 498041685-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amideYield 81%

Procedure

As described for example 31, 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (75 mg, 0.2 mmol) was converted, using 2,2,2-trifluoroethylamine instead of 1,1,1-trifluoro-isopropylamine, to the title compound (70 mg, 81%), which was obtained as a colourless gum. MS: m/e=426.2 [M+H]+.

Sources & evidence

ORD record
ord-2f7c2ab66f7d44838497e48543aedd05
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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