1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 44185125, compound

HRID 1864644Notes

Reaction equation

HRID 1864644 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][C:14](=[O:16])[NH:15][C:8]=23)=[CH:4][C:3]=1[F:19].[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]>>[O:16]=[C:14]1[NH:13][C:9]2=[N:10][CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:17]=[CH:18][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])=[C:3]([F:19])[CH:4]=3)=[C:8]2[NH:15]1

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 44184950HCID 44184950, compound

Product 1

HCID 44185125HCID 44185125, compoundYield 83%

Procedure

Method H2 was used with 7-(4-amino-3-fluorophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (26 mg, 0.1 mmol) and 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (23 mg, 0.1 mmol) to afford the title compound (40 mg, 83%). 1H-NMR (δ, ppm, DMSO-d6): 6.45 (d, 1H, HPy,5, J=5.91 Hz), 6.98 (d, 1H, Harom,Ph), 7.23 (d, 1H, Harom,Ph), 7.63 (broad s, 2H, Harom), 7.79 (d, 1H, HPy,6), 8.05 (s, 1H, Harom,Ph), 8.12 (s, 1H, Harom′), 8.69 (s, 1H, NHurea,1), 9.49 (s, 1H, NHurea,3), 11.22 (s, 1H, NHPy3), 11.42 (s, 1H, NHPy2). LC-MS (m/z): 481 (M+H, 100).

Sources & evidence

ORD record
ord-1b5ebaaa14ee4a9696db369fa21055e9
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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