4-(Trifluoromethyl)phenyl isocyanate → Methyl-3-methyl-2-(4-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl) thiazole-2-carboxamido)butanoate

HRID 1024453Notes

Reaction equation

HRID 1024453 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[C:2]=[O:3].[CH3:14][CH:15]([CH3:38])[CH:16]([NH:21][C:22]([C:24]1[S:25][CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=2)[N:28]=1)=[O:23])[C:17]([O:19][CH3:20])=[O:18]>>[CH3:20][O:19][C:17](=[O:18])[CH:16]([NH:21][C:22]([C:24]1[S:25][CH:26]=[C:27]([C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:2]([NH:1][C:4]3[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:9]=3)=[O:3])=[CH:33][CH:34]=2)[N:28]=1)=[O:23])[CH:15]([CH3:38])[CH3:14]

Participants

3

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52935054Methyl-3-methyl-2-(4-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl) thiazole-2-carboxamido)butanoateYield 79%

Procedure

The title compound was synthesized analogous to Example 23, using 1-isocyanato-4-(trifluoromethyl)benzene and intermediate 3. Yield: 79%; 1H NMR (DMSO-d6, 300 MHz): δ 9.14 (s, 1H), 8.99 (s, 1H), 8.80 (d, 1H), 8.32 (s, 1H), 8.06 (d, 2H), 7.66 (bs, 4H), 7.61 (d, 2H), 4.37 (s, 1H), 3.70 (s, 3H), 2.32 (m, 1H), 0.97 (s, 6H).

Sources & evidence

ORD record
ord-f194bd948f8c4093835526bee5e86cf8
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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