1-(4-Amino-3-fluorophenyl)pyridin-2-one → HCID 16066155, compound

HRID 2244675Notes

Reaction equation

CO[C:3]([C@H:5]1[CH2:9][C@H:8]([O:10][CH3:11])[C@@H:7]([NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[CH2:6]1)=[O:4].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]2=[O:34])=[CH:24][C:23]=1[F:35]>>[F:35][C:23]1[CH:24]=[C:25]([N:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]2=[O:34])[CH:26]=[CH:27][C:22]=1[NH:21][C:3]([C@@H:5]1[CH2:6][C@H:7]([NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[C@@H:8]([O:10][CH3:11])[CH2:9]1)=[O:4]

Participants

Reactant 2

HCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-one

HCID 58826460HCID 58826460, compound

Product 1

HCID 16066155HCID 16066155, compound

Procedure

In analogy to example 1C, (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-cyclopentanecarboxylic acid methyl ester was reacted with 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one to give 5-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-2-methoxy-cyclopentyl}-amide. Light yellow amorphous solid. MS: 490.1 ([M+H]+).

Sources & evidence

ORD record: ord-89ac80d925574f80863ae9b26422e5b9
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678917B2

Reaction notes

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