4-Chlorophenyl Isocyanate → (S)-Methyl 2-(5-(4-(3-(4-chlorophenyl)ureido)phenyl)oxazole-2-carboxamido)-3-methylbutanoate

HRID 1024463Notes

Reaction equation

HRID 1024463 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29][CH3:30])=[O:28])=[O:24])=[N:20][CH:19]=2)=[CH:14][CH:13]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:22][C:21]([C:23]([NH:25][C@@H:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29][CH3:30])=[O:28])=[O:24])=[N:20][CH:19]=3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 67150345Methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate

Product 1

HCID 52932714(S)-Methyl 2-(5-(4-(3-(4-chlorophenyl)ureido)phenyl)oxazole-2-carboxamido)-3-methylbutanoate

Procedure

The title compound was synthesized analogous to Example 1, using 1-chloro-4-isocyanatobenzene (0.533 mmol) and intermediate 1. 1H NMR (DMSO-d6, 300 MHz): δ 9.011-8.983 (d, 2H), 8.919 (s, 1H), 7.813 (s, 1H), 7.792-7.763 (d, J=8.7 Hz, 2H), 7.624-7.595 (d, J=8.7 Hz, 2H), 7.518-7.488 (d, J=9 Hz, 2H), 7.357-7.327 (d, J=9 Hz, 2H), 4.327-4.276 (m, 1H), 3.680 (s, 3H), 2.285-2.216 (m, 1H), 0.979-0.957 (d, J=6.6 Hz, 6H); MS (ESI) m/z 471 (M+H)+.

Sources & evidence

ORD record
ord-3cc1238bbe69467cbd09fccf247e465b
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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