4-(4-Amino-3-fluorophenyl)morpholin-3-one → 3-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid [2-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-amide

HRID 2237644Notes

Reaction equation

HRID 2237644 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[N:7]=1)=[O:5])C.[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][C:23]=1[F:35]>>[F:35][C:23]1[CH:24]=[C:25]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][C:29]2=[O:34])[CH:26]=[CH:27][C:22]=1[NH:21][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[N:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 534177984-(4-Amino-3-fluorophenyl)morpholin-3-oneHCID 593029563-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

Product 1

HCID 249676313-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid [2-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-amide

Procedure

In analogy to example 1E 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (example 1D) was reacted with 4-(4-amino-3-fluoro-phenyl)-morpholin-3-one (CAS 742073-22-9) to give 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid [2-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-amide. Light yellow solid. MS 480.0 ([M+H]+)

Sources & evidence

ORD record
ord-5356ea9ec66741a7827e0d6d8246f7f0
Source dataset
uspto-grants-2010_05
Patent number
US07718679B2

Reaction notes

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