1-Hydroxycyclobutanecarboxylic acid → (S)-N-(3-(2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenyl)-1-hydroxycyclobutanecarboxamide

HRID 2409198Notes

Reaction equation

HRID 2409198 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.[OH:28][C:29]1([C:33](O)=[O:34])[CH2:32][CH2:31][CH2:30]1>>[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:33]([C:29]3([OH:28])[CH2:32][CH2:31][CH2:30]3)=[O:34])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 109534701-Hydroxycyclobutanecarboxylic acidHCID 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 66727558(S)-N-(3-(2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenyl)-1-hydroxycyclobutanecarboxamide

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 F) and 1-hydroxy-cyclobutanecarboxylic acid followed by deprotection of the intermediate yielded the title compound as a colorless amorphous solid. MS (ESI): m/z=377.4 [M+H]+.

Sources & evidence

ORD record
ord-d18aefcdb93d4c0c95a63a337d69559e
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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