1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 44186295, compound

HRID 1864642Notes

Reaction equation

HRID 1864642 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[NH:19][C:20](=[O:22])[NH:21][C:14]=23)=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[NH:19][C:20](=[O:22])[NH:21][C:14]=34)=[CH:4][CH:3]=2)=[O:32])=[CH:26][C:25]=1[C:33]([F:34])([F:35])[F:36]

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 44186026HCID 44186026, compound

Product 1

HCID 44186295HCID 44186295, compoundYield 15.2%

Procedure

Method H2 was used with 7-(4-aminonaphthalen-1-yl-oxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (94 mg, 0.32 mmol) and 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (77 mg, 0.35 mmol) to afford the title compound as a brown solid (25 mg, 15%). 1H-NMR (6, ppm, DMSO-d6): 6.21 (d, 1H, HPy,5, J=5.9 Hz), 7.20 (m, 1H, Harom,Naph), 7.56-7.67 (m, 4H, Harom,naph+Py,6), 7.79-7.87 (m, 2H, Harom,Ph′), 7.94-7.97 (m, 1H, Harom,naph), 8.23-8.31 (m, 2H, Harom,naph), 10.52 (s, NH, NHPy), 11.26 (s, NH, NHPy). LC-MS (m/z): 514 (M+H, 100).

Sources & evidence

ORD record
ord-fceb279f084c4ee7a42a2da8cb9226c7
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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