3-(Trifluoromethyl)phenyl isocyanate → HCID 44185067, compound

HRID 1864643Notes

Reaction equation

HRID 1864643 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.[N:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1)=[C:24]=[O:25]>>[O:22]=[C:20]1[NH:19][C:15]2=[N:16][CH:17]=[CH:18][C:13]([O:12][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2]([NH:1][C:24]([NH:23][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=4)=[O:25])=[CH:3][CH:4]=3)=[C:14]2[NH:21]1

Participants

3

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 44186026HCID 44186026, compound

Product 1

HCID 44185067HCID 44185067, compoundYield 65%

Procedure

Method H2 was used with 7-(4-aminonaphthalen-1-yl-oxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (30 mg, 0.10 mmol) and 1-isocyanato-3-(trifluoromethyl)benzene (21 mg, 0.11 mmol) to afford the title compound as a brown solid (31 mg, 65%). 1H-NMR (δ, ppm, DMSO-d6): 6.21 (d, 1H, HPy,5, J=5.5 Hz), 7.32 (m, 2H, Harom,Naph), 7.53-7.71 (m, 5H, Harom,naph+Ph′), 7.96 (t, 2H, Harom,naph), 8.09 (s, 1H, Harom,Ph), 8.19 (d, 1H, HPy,6, J=5.5 Hz), 8.96 and 9.46 (bs, 2H, NHurea) 11.39 (s, NH, NHPy), 11.44 (s, NH, NHPy). LC-MS (m/z): 480 (M+H, 100).

Sources & evidence

ORD record
ord-afaea6d7d01f4b968abc42276d6ff028
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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