3-(Trifluoromethyl)benzoyl chloride → HCID 58024347, compound

HRID 552407Notes

Reaction equation

HRID 552407 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:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>>[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:24](=[O:25])[C:23]4[CH:27]=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 58024347HCID 58024347, compoundYield 32%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-(trifluoromethyl)benzoyl chloride to afford the title compound as an off-white solid (17 mg, 32%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=6.0 Hz), 6.94 (d, 1H, Harom, J=8.0 Hz), 7.44 (ps t, 1H, Harom, J=8.0 Hz), 7.62 (s, 1H, Harom), 7.66 (d, 1H, Harom, J=7.5 Hz), 7.72-7.82 (m, 2H, Harom+Py,6), 7.96 (d, 1H, Harom, J=8.0 Hz), 8.24 (d, 1H, Harom, J=7.5 Hz), 8.26 (s, 1H, Harom), 10.55 (s, 1H, NHamide), 11.20 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.62, 110.87, 113.79, 114.73, 116.37, 123.93, 124.26, 128.28, 129.19, 129.75, 130.25, 131.85, 135.54, 140.48, 141.35, 144.55, 147.17, 154.21, 154.78, 164.22. HRMS (EI): m/z [M+H] calcd for C20H14F3N4O3: 415.1018; found: 415.1010.

Sources & evidence

ORD record
ord-a225f57a84b44be49007a1eabf38e82b
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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