3-(Trifluoromethoxy)benzoyl chloride → HCID 45141328, compound

HRID 552411Notes

Reaction equation

HRID 552411 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:32])([F:31])[O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>>[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][CH:30]=[C:22]([O:21][C:20]([F:19])([F:31])[F:32])[CH:23]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141328HCID 45141328, compoundYield 64%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-(trifluoromethoxy)benzoyl chloride to afford the title compound as an off-white solid (36 mg, 64%). 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 (ps t, 1H, Harom, J=8.0 Hz), 7.62 (s, 1H, Harom), 7.64-7.69 (m, 3H, Harom), 7.81 (d, 1H, HPy,6, J=6.0 Hz), 7.88 (s, 1H, Harom), 7.99 (d, 1H, Harom, J=8.0 Hz), 10.47 (s, 1H, NHamide), 11.20 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.61, 110.86, 113.78, 114.72, 116.36, 120.05, 121.07, 124.17, 126.80, 130.23, 130.64, 136.83, 140.47, 141.35, 144.55, 147.17, 148.28, 154.21, 154.76, 164.03. HRMS (EI): m/z [M+H] calcd for C20H14F3N4O4: 431.0967; found: 431.0968.

Sources & evidence

ORD record
ord-981591ae4821415695e085439d0378d4
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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