2-Chloro-4-(trifluoromethyl)phenyl isocyanate → HCID 52933906, compound

HRID 1024474Notes

Reaction equation

HRID 1024474 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].[CH3:15][CH:16]([CH3:39])[CH:17]([NH:22][C:23]([C:25]1[S:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=2)[N:29]=1)=[O:24])[C:18]([O:20][CH3:21])=[O:19]>>[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:36][C:33]1[CH:34]=[CH:35][C:30]([C:28]2[N:29]=[C:25]([C:23]([NH:22][C@@H:17]([CH:16]([CH3:39])[CH3:15])[C:18]([O:20][CH3:21])=[O:19])=[O:24])[S:26][CH:27]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 51025332-Chloro-4-(trifluoromethyl)phenyl isocyanateHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52933906HCID 52933906, compound

Procedure

The title compound was synthesized analogous to Example 23, using 2-chloro-4-(trifluoromethyl)-1-isocyanatobenzene and intermediate 3. 1HNMR (DMSO-d6, 300 MHz): δ 9.801 (s, 1H), 8.832-8.804 (d, J=8.4 Hz, 1H), 8.680 (s, 1H), 8.515-8.486 (d, J=8.7 Hz, 1H), 8.348 (s, 1H), 8.095-8.067 (d, J=8.4 Hz, 2H), 7.897-7.893 (d, J=1.2 Hz, 2H), 7.721-7.686 (dd, J=1.8, 9 Hz, 1H), 7.621-7.593 (d, J=8.4 Hz, 2H), 4.401-4.344 (t, J=8.1, 9 Hz, 1H), 3.702 (s, 3H), 2.351-2.280 (m, 1H), 1.003-0.955 (t, J=7.2 Hz, 6H); MS (ESI) m/z 553 (M−H), 555 (M+H)+.

Sources & evidence

ORD record
ord-d18723af0e0d4d9bbfad272963e977c7
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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