1-(4-Aminophenyl)pyrazin-2(1H)-one → HCID 16066160, compound

HRID 2244667Notes

Reaction equation

HRID 2244667 reaction equation
CO[C:3]([C@H:5]1[CH2:9][C@H:8]([OH:10])[C@@H:7]([NH:11][C:12]([C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:13])[CH2:6]1)=[O:4].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]2=[O:33])=[CH:23][CH:22]=1>>[OH:10][C@H:8]1[CH2:9][C@H:5]([C:3](=[O:4])[NH:20][C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH:32]=[CH:31][N:30]=[CH:29][C:28]3=[O:33])=[CH:25][CH:26]=2)[CH2:6][C@@H:7]1[NH:11][C:12]([C:14]1[S:15][C:16]([Cl:19])=[CH:17][CH:18]=1)=[O:13]

Participants

3

Reactant 2

HCID 230867681-(4-Aminophenyl)pyrazin-2(1H)-oneHCID 58826431(1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 16066160HCID 16066160, compound

Procedure

In analogy to example 1C, (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester (example 1B) was reacted with 1-(4-aminophenyl)-1H-pyrazin-2-one (CAS 444002-64-6) to give 5-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-2-hydroxy-4-[4-(2-oxo-2H-pyrazin-1-yl)-phenylcarbamoyl]-cyclopentyl}-amide. Light yellow solid. MS: 459.3 ([M+H]+)

Sources & evidence

ORD record
ord-98b30e6f0db94afb99c29849eaa2ae4a
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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