4-(4-Aminophenyl)morpholin-3-one → 5-chloro-thiophene-2-carboxylic acid ((3S,4S)-4-methoxy-1-{[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-methyl}-pyrrolidin-3-yl)-amide

HRID 1162638Notes

Reaction equation

HRID 1162638 reaction equation
C(O[C:4](=[O:22])[CH2:5][N:6]1[CH2:10][C@H:9]([O:11][CH3:12])[C@@H:8]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:7]1)C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C:31]2=[O:36])=[CH:26][CH:25]=1>>[CH3:12][O:11][C@H:9]1[CH2:10][N:6]([CH2:5][C:4](=[O:22])[NH:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C:31]3=[O:36])=[CH:28][CH:29]=2)[CH2:7][C@@H:8]1[NH:13][C:14]([C:16]1[S:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:15]

Participants

3

Reactant 2

HCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 58748327{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester

Product 1

HCID 587483195-chloro-thiophene-2-carboxylic acid ((3S,4S)-4-methoxy-1-{[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-methyl}-pyrrolidin-3-yl)-amide

Procedure

Using general procedure F {(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester (example 25.2) was reacted with 4-(4-aminophenyl)-morpholin-3-one (CAS 438056-69-0) to give 5-chloro-thiophene-2-carboxylic acid ((3S,4S)-4-methoxy-1-{[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-methyl}-pyrrolidin-3-yl)-amide. Yellow solid. MS 493.0 ([M+H]+)

Sources & evidence

ORD record
ord-a9e3fb7eac5b4aaf891d64c1a3a65c56
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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