2-Chloro-4-(trifluoromethyl)phenyl isocyanate → (S)-methyl 2-(5-(4-(3-(2-chloro-4-(trifluoromethyl)phenyl)ureido) phenyl)oxazole-2-carboxamido)-3-methylbutanoate

HRID 1024465Notes

Reaction equation

HRID 1024465 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]=[C:13]=[O:14].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:26][C:25]([C:27]([NH:29][CH:30]([CH:35]([CH3:37])[CH3:36])[C:31]([O:33][CH3:34])=[O:32])=[O:28])=[N:24][CH:23]=2)=[CH:18][CH:17]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:14])[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:26][C:25]([C:27]([NH:29][C@@H:30]([CH:35]([CH3:37])[CH3:36])[C:31]([O:33][CH3:34])=[O:32])=[O:28])=[N:24][CH:23]=2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 51025332-Chloro-4-(trifluoromethyl)phenyl isocyanateHCID 67150345Methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate

Product 1

HCID 52932941(S)-methyl 2-(5-(4-(3-(2-chloro-4-(trifluoromethyl)phenyl)ureido) phenyl)oxazole-2-carboxamido)-3-methylbutanoate

Procedure

The title compound was synthesized analogous to Example 1, using 2-chloro-4-(trifluoromethyl)-1-isocyanatobenzene (0.533 mmol) and intermediate 1. 1H NMR (DMSO-d6, 300 MHz): δ 9.883 (s, 1H), 9.025-8.998 (d, 1H), 8.707 (s, 1H), 8.498-8.469 (d, J=8.7 Hz, 1H), 7.904-7.898 (d, J=1.8 Hz, 1H), 7.842 (s, 1H), 7.837-7.807 (d, J=9 Hz, 2H), 7.723-7.688 (dd, J=1.8, 9 Hz, 1H), 7.653-7.624 (d, J=8.7 Hz, 2H), 4.332-4.2827 (m, 1H), 3.682 (s, 3H), 2.228-2.219 (m, 1H), 0.982-0.960 (d, J=6.6 Hz, 6H); MS (ESI) m/z 537 (M−H), 539 (M+H).

Sources & evidence

ORD record
ord-d28b5f1c9a6c46e594f54de119de9276
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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