Benzoyl chloride → N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)benzamide

HRID 552409Notes

Reaction equation

HRID 552409 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.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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:19](=[O:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45140726N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)benzamideYield 82%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and benzoyl chloride to afford the title compound as an off-white solid (37 mg, 82%). 1H-NMR (□, ppm, DMSO-d6): 6.49 (d, 1H, HPy,5, J=6.0 Hz), 6.90 (d, 1H, Harom, J=8.0 Hz), 7.42 (ps t, 1H, Harom, J=8.0 Hz), 7.51-7.68 (m, 5H, Harom), 7.81 (d, 1H, HPy,6, J=6.0 Hz), 7.93 (d, 2H, Harom, J=7.5 Hz), 10.35 (s, 1H, NHamide), 11.20 (s, 1H, NHPy3), 11.40 (s, 1H, NHPy2). 13C-NMR (□, ppm, DMSO-d6): 106.56, 110.71, 114.34, 116.20, 127.64, 128.37, 129.32, 130.13, 131.69, 134.68, 140.88, 141.26, 144.65, 147.10, 154.19, 154.69, 165.72. HRMS (EI): m/z [M+H] calcd for C19H15N4O3: 347.1144; found: 347.1140.

Sources & evidence

ORD record
ord-cc44b11711884716a88c16eec08cdf43
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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