4-(4-Amino-3-fluorophenyl)morpholin-3-one → HCID 16066320, compound

HRID 2244665Notes

Reaction equation

HRID 2244665 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[CH2:32][CH2:31][O:30][CH2:29][C:28]2=[O:33])=[CH:23][C:22]=1[F:34]>>[F:34][C:22]1[CH:23]=[C:24]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][C:28]2=[O:33])[CH:25]=[CH:26][C:21]=1[NH:20][C:3]([C@@H:5]1[CH2:6][C@H:7]([NH:11][C:12]([C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:13])[C@@H:8]([OH:10])[CH2:9]1)=[O:4]

Participants

3

Reactant 2

HCID 534177984-(4-Amino-3-fluorophenyl)morpholin-3-oneHCID 58826431(1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 16066320HCID 16066320, 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 4-(4-amino-3-fluoro-phenyl)-morpholin-3-one (CAS 438056-69-0) to give 5-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-4-[2-fluoro-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-2-hydroxy-cyclo-pentyl}-amide. Yellow solid. MS: 482.3 ([M+H]+)

Sources & evidence

ORD record
ord-6c5352cd648f45b88b2251de0bfef1b2
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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