Ethanamine, 2,2,2-trifluoro- → HCID 46897454, compound

HRID 1920949Notes

Reaction equation

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

Participants

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-

HCID 67492207HCID 67492207, compound

Product 1

HCID 46897454HCID 46897454, compoundYield 21%

Procedure

As described for example 43 g, 3-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.29 mmol) was converted, using 2,2,2-trifluoroethylamine instead of isopropylamine, to the title compound (25 mg, 21%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol=1:0 to 9:1). MS: m/e=414.0 [M−H]−.

Sources & evidence

ORD record: ord-9e6065d5f3404031a029dc8226230513
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173652B2

Reaction notes

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