Chlorophenyl isocyanate → Methyl 2-(5-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024442

Reaction equation

HRID 1024442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[CH3:11][CH:12]([CH3:35])[CH:13]([NH:18][C:19]([C:21]1[S:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)=[CH:24][N:25]=1)=[O:20])[C:14]([O:16][CH3:17])=[O:15]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:10])[NH:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[S:22][C:21]([C:19]([NH:18][CH:13]([CH:12]([CH3:35])[CH3:11])[C:14]([O:16][CH3:17])=[O:15])=[O:20])=[N:25][CH:24]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52934365Methyl 2-(5-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoateYield 87%

Procedure

The title compound was synthesized analogous to Example 9, using 1-chloro-2-isocyanatobenzene and intermediate 2. Yield: 87%; 1HNMR (DMSO-d6, 300 MHz): δ 9.67 (s, 1H), 8.74 (d, 1H), 8.38 (s, 1H), 8.36 (s, 1H), 8.15 (dd, 1H), 7.75 (d, 2H), 7.6 (d, 2H), 7.49 (dd, 1H), 7.32 (m, 1H), 7.06 (m, 1H), 4.33, (m, 1H), 3.68 (s, 3H), 2.26 (m, 1H), 0.95 (d, 6H); MS (ES+): m/z 487 (M+1).

Sources & evidence

ORD record
ord-eff5040455484273aebb7c21b6c56f8d
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Linked notes

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