4-Chloro-2-phenoxyphenyl isocyanate → Methyl 2-(5-(4-(3-(4-chloro-2-phenoxyphenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024444Notes

Reaction equation

HRID 1024444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[CH3:18][CH:19]([CH3:42])[CH:20]([NH:25][C:26]([C:28]1[S:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=2)=[CH:31][N:32]=1)=[O:27])[C:21]([O:23][CH3:24])=[O:22]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:39][C:36]2[CH:37]=[CH:38][C:33]([C:30]3[S:29][C:28]([C:26]([NH:25][CH:20]([CH:19]([CH3:42])[CH3:18])[C:21]([O:23][CH3:24])=[O:22])=[O:27])=[N:32][CH:31]=3)=[CH:34][CH:35]=2)=[C:4]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 34074334-Chloro-2-phenoxyphenyl isocyanateHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52934594Methyl 2-(5-(4-(3-(4-chloro-2-phenoxyphenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoateYield 60%

Procedure

The title compound was synthesized analogous to Example 9, using 4-chloro-1-isocyanato-2-phenoxybenzene and intermediate 2. Yield: 60%; 1HNMR (DMSO-d6, 300 MHz): δ 9.61 (s, 1H), 8.73 (s, 1H), 8.71 (d, 1H), 8.4 (d, 1H), 8.36 (s, 1H), 7.74 (d, 2H), 7.54 (d, 2H), 7.44 (d, 2H), 7.2 (dd, 1H), 7.11 (d, 2H), 7.03 (dd, 1H), 6.86 (d, 1H), 4.33, (m, 1H), 3.68 (s, 3H), 2.26 (m, 1H), 0.95 (d, 6H); MS (ES+) m/z 579 (M+1).

Sources & evidence

ORD record
ord-3bc6f6673ba74e30b786571cdea231f9
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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