3,4-Dimethylphenyl isocyanate → Methyl 2-(4-(4-(3-(3,4-dimethylphenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024454Notes

Reaction equation

HRID 1024454 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([CH3:11])[CH:5]=1)=[C:2]=[O:3].[CH3:12][CH:13]([CH3:36])[CH:14]([NH:19][C:20]([C:22]1[S:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=2)[N:26]=1)=[O:21])[C:15]([O:17][CH3:18])=[O:16]>>[CH3:11][C:6]1[CH:5]=[C:4]([NH:1][C:2](=[O:3])[NH:33][C:30]2[CH:31]=[CH:32][C:27]([C:25]3[N:26]=[C:22]([C:20]([NH:19][CH:14]([CH:13]([CH3:36])[CH3:12])[C:15]([O:17][CH3:18])=[O:16])=[O:21])[S:23][CH:24]=3)=[CH:28][CH:29]=2)[CH:9]=[CH:8][C:7]=1[CH3:10]

Participants

3

Reactant 2

HCID 43896633,4-Dimethylphenyl isocyanateHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52935265Methyl 2-(4-(4-(3-(3,4-dimethylphenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoateYield 75%

Procedure

The title compound was synthesized analogous to Example 23, using 4-isocyanato-1,2-dimethylbenzene and intermediate 3. Yield: 75%; 1H NMR (DMSO-d6, 300 MHz): δ 8.80 (s, 2H), 8.51 (s, 1H), 8.30 (s, 1H), 8.03 (d, 2H), 7.57 (d, 2H), 7.24 (s, 1H), 7.19 (d, 1H), 7.07 (d, 1H), 4.39 (t, 1H), 3.70 (s, 3H), 2.31 (m, 1H), 2.19 (s, 3H), 2.16 (s, 3H), 0.97 (t, 6H).

Sources & evidence

ORD record
ord-8885298544244ad3b1dbbbbf041a3d43
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

Loading…