4-(Trifluoromethyl)benzoyl chloride → HCID 45141110, compound

HRID 552413Notes

Reaction equation

HRID 552413 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][C:13](=[O:15])[NH:14][C:7]=12.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>>[O:15]=[C:13]1[NH:12][C:8]2=[N:9][CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:25](=[O:26])[C:24]4[CH:28]=[CH:29][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141110HCID 45141110, compoundYield 61%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 4-(trifluoromethyl)benzoyl chloride to afford the title compound as a brown solid (33 mg, 61%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=6.0 Hz), 6.93 (d, 1H, Harom, J=7.0 Hz), 7.44 (t, 1H, Harom, J=8.0 Hz), 7.63 (s, 1H, Harom), 7.64-7.68 (m, 1H, Harom), 7.82 (d, 1H, HPy,6, J=6.0 Hz), 7.91 (d, 2H, Harom, J=8.0 Hz), 8.12 (d, 2H, Harom, J=8.0 Hz), 10.55 (s, 1H, NHamide), 11.20 (s, 1H, NHPy3), 11.38 (s, 1H, NHPy2).

Sources & evidence

ORD record
ord-33fcaf716a8042408c3422f91ee12d4e
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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