1,1,1-Trifluoro-2-propanamine → 5-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2h-pyrazole-3-carboxylic acid ((s)-2,2,2-trifluoro-1-methyl-ethyl)-amide

HRID 1695448Notes

Reaction equation

HRID 1695448 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:26])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4].[CH3:27][CH:28]([NH2:33])[C:29]([F:32])([F:31])[F:30]>>[F:30][C:29]([F:32])([F:31])[C@@H:28]([NH:33][C:3]([C:5]1[N:6]([CH3:26])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4])[CH3:27]

Participants

3

Reactant 2

HCID 37831651,1,1-Trifluoro-2-propanamineHCID 666439315-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 497930915-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2h-pyrazole-3-carboxylic acid ((s)-2,2,2-trifluoro-1-methyl-ethyl)-amideYield 17%

Procedure

As described for example 100f, 5-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.27 mmol) was converted, using L-2,2,2-trifluoro-1-(methyl)ethylamine instead of isopropylamine, to the title compound (21 mg, 17%) which was obtained as a colorless gum. MS: m/e=459.3 [M+H]+.

Sources & evidence

ORD record
ord-e3268f7c443e46eaac2f8cd3a88ad9ba
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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