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

HRID 1695435Notes

Reaction equation

HRID 1695435 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]([F:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4].[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]([F:25])=[CH:23][CH:24]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 66643735HCID 66643735, compound

Product 1

HCID 595684865-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2,2,3,3,3-pentafluoro-propyl)-amideYield 87%

Procedure

As described for example 91h, 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.28 mmol) was converted, using 2,2,3,3,3-pentafluoropropylamine instead of 4-aminotetrahydropyran, to the title compound (115 mg, 87%) which was obtained as a brown oil. MS: m/e=477.0 [M−]−.

Sources & evidence

ORD record
ord-868d6342f6f845f1a0332523cb592bdd
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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