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

HRID 600493Notes

Reaction equation

HRID 600493 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]2[C:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:15][O:16][CH:17]=2)=[CH:7][N:6]=1)=[O:4].COC(C1C=NC(NCC2C(C3C=CC=CC=3)=NOC=2C)=CN=1)=O.[F:49][C:50]([F:54])([F:53])[CH2:51][NH2:52]>>[F:49][C:50]([F:54])([F:53])[CH2:51][NH:52][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]2[C:14]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[N:15][O:16][CH:17]=2)=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 684456305-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl esterHCID 684464005-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 469378495-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amideYield 71%

Procedure

As described for example 9b, 5-[3-(4-fluoro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester (75 mg, 0.23 mmol), instead of 5-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester, was converted, using 2,2,2-trifluoroethylamine instead of isopropylamine, to the title compound (64 mg, 71%) which was obtained as a light yellow solid. MS: m/e=397.2 [M+H]+.

Sources & evidence

ORD record
ord-98ccd88501354624ba8dcd9d9699f8cd
Source dataset
uspto-grants-2011_03
Patent number
US07902201B2

Reaction notes

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