1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 11719900, compound
Reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[N:13]([CH3:17])[C:14](=[O:16])[NH:15][C:8]=23)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>>[CH3:17][N:13]1[C:9]2=[N:10][CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:18]=[CH:19][C:2]([NH:1][C:28]([NH:27][C:24]4[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:32])([F:31])[F:33])[CH:23]=4)=[O:29])=[CH:3][CH:4]=3)=[C:8]2[NH:15][C:14]1=[O:16]Participants
3
Procedure
Method H2 was used with 7-(4-aminophenoxy)-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (20 mg, 0.08 mmol) and 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (17 mg, 0.08 mmol) to afford the title compound as a solid (32 mg, 84%). 1H-NMR (δ, ppm, DMSO-d6): 3.30 (s, 3H, CH3), 6.40 (d, 1H, HPy,5, J=5.55 Hz), 7.13 (d, 2H, Harom,Ph,3+5, J=8.05 Hz), 7.54 (d, 2H, Harom,Ph,2+6), 7.61-7.65 (m, 2H, Harom′), 7.84 (d, 1H, HPy,6), 8.11 (s, 1H, Harom′), 8.97 (s, 1H, NHurea1), 9.20 (s, 1H, NHurea,3), 11.48 (s, 1H, NHPy3).
Sources & evidence
- ORD record
- ord-6598ca423c894bdbb7cfa924044b79a5
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625922B2
Reaction notes
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