4-(4-Aminophenyl)morpholin-3-one → 5-chloro-thiophene-2-carboxylic acid {(1RS,2SR,4SR)-2-hydroxy-4-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-cyclopentylmethyl}-amide

HRID 2244680Notes

Reaction equation

HRID 2244680 reaction equation
CO[C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]([CH2:11][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[CH2:33][CH2:32][O:31][CH2:30][C:29]2=[O:34])=[CH:24][CH:23]=1>>[OH:10][CH:8]1[CH2:9][CH:5]([C:3](=[O:4])[NH:21][C:22]2[CH:23]=[CH:24][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C:29]3=[O:34])=[CH:26][CH:27]=2)[CH2:6][CH:7]1[CH2:11][NH:12][C:13]([C:15]1[S:16][C:17]([Cl:20])=[CH:18][CH:19]=1)=[O:14]

Participants

3

Reactant 2

HCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 68687973(1SR,3RS,4SR)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-hydroxy-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 732308805-chloro-thiophene-2-carboxylic acid {(1RS,2SR,4SR)-2-hydroxy-4-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-cyclopentylmethyl}-amide

Procedure

In analogy to example 15C, (1SR,3RS,4SR)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-hydroxy-cyclopentanecarboxylic acid methyl ester was reacted with 4-(4-amino-phenyl)-morpholin-3-one (CAS 438056-69-0) to give 5-chloro-thiophene-2-carboxylic acid {(1RS,2SR,4SR)-2-hydroxy-4-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-cyclopentylmethyl}-amide. Orange solid. MS: 478.3 ([M+H]+).

Sources & evidence

ORD record
ord-7401fd1b1c4149a1a5328fe60717a98c
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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