2H-Hexafluoro(2-methylpropanoic acid) → N-[3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenyl]-3,3,3-trifluoro-2-trifluoromethyl-propionamide

HRID 2409133Notes

Reaction equation

HRID 2409133 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]([CH3:26])[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[C@:12]([C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)(C)(C)C.[F:28][C:29]([F:39])([F:38])[CH:30]([C:34]([F:37])([F:36])[F:35])[C:31](O)=[O:32]>>[NH2:7][C:8]1[N:9]([CH3:26])[C:10](=[O:25])[C:11]([CH3:23])([CH3:24])[C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:31](=[O:32])[CH:30]([C:29]([F:38])([F:28])[F:39])[C:34]([F:37])([F:36])[F:35])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 3856062H-Hexafluoro(2-methylpropanoic acid)HCID 57496584[(S)-4-(5-amino-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester2×

Product 1

HCID 86661860N-[3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenyl]-3,3,3-trifluoro-2-trifluoromethyl-propionamide

Procedure

The coupling of [(S)-4-(5-amino-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (intermediate F2) and 3,3,3-trifluoro-2-trifluoromethyl-propionic acid followed by deprotection of the intermediate yielded the title compound as a white solid. MS (ESI): m/z=457.3 [M+H]+.

Sources & evidence

ORD record
ord-9e4747cbc34144a2999f80dd401ddb67
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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