2,2,3,3,3-Pentafluoropropylamine → 5-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2,2,3,3,3-pentafluoro-propyl)-amide

HRID 1695446Notes

Reaction equation

HRID 1695446 reaction equation
C[O:2][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.[F:27][C:28]([F:35])([C:31]([F:34])([F:33])[F:32])[CH2:29][NH2:30]>>[F:27][C:28]([F:35])([C:31]([F:34])([F:33])[F:32])[CH2:29][NH:30][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:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:2]

Participants

3

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 666439315-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 497931115-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2,2,3,3,3-pentafluoro-propyl)-amideYield 26%

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 2,2,3,3,3-pentafluoropropylamine instead of isopropylamine, to the title compound (35 mg, 26%) which was obtained as a white solid. MS: m/e=495.1 [M+H]+.

Sources & evidence

ORD record
ord-7ea164b7fcb5497e80f819d38a4ee379
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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