1,1,1-Trifluoro-2-propanamine → 2-[(e)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid ((r)-2,2,2-trifluoro-1-methyl-ethyl)-amide

HRID 1923622Notes

Reaction equation

HRID 1923622 reaction equation
[CH2:1]([C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:22][CH:23]([NH2:28])[C:24]([F:27])([F:26])[F:25]>>[F:25][C:24]([F:27])([F:26])[C@H:23]([NH:28][C:18]([C:14]1[S:13][C:12](/[CH:11]=[CH:10]/[C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:21])=[N:16][C:15]=1[CH3:17])=[O:20])[CH3:22]

Participants

3

Reactant 2

HCID 37831651,1,1-Trifluoro-2-propanamineHCID 595685392-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 497813682-[(e)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid ((r)-2,2,2-trifluoro-1-methyl-ethyl)-amideYield 46%

Procedure

As described for example 104, 2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (153 mg, 0.5 mmol) was converted, using L-2,2,2,-trifluoro-1-(methyl)ethylamine instead of rac-2-amino-1-butanol, to the title compound (92 mg, 46%) which was obtained as a white solid after purification by chromatography (silica, 50 to 100% ethyl acetate in heptane and recrystallization from ethyl acetate/heptane. MS: m/e=402.3 [M+H]+.

Sources & evidence

ORD record
ord-773e29197d0b43ec98911685462b2c95
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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