Benzenepropanoyl chloride → HCID 45141325, compound

HRID 552424Notes

Reaction equation

HRID 552424 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]1([CH2:25][CH2:26][C:27](Cl)=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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:27](=[O:28])[CH2:26][CH2:25][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141325HCID 45141325, compoundYield 19%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-phenylpropanoyl chloride to afford the title compound (15 mg, 19%). 1H-NMR (δ, ppm, DMSO-d6): 2.61 (t, 2H, CH2, J=8.0 Hz), 2.89 (t, 2H, CH2, J=8.0 Hz), 6.45 (d, 1H, HPy,5, J=6.0 Hz), 6.82 (d, 1H, Harom, J=8.0 Hz), 7.16-7.44 (m, 8H, Harom), 7.79 (d, 1H, HPy,6, J=6.0 Hz), 10.02 (s, 1H, NHamide), 11.16 (s, 1H, NHPy3), 11.37 (s, 1H, NHPy2). HRMS (EI): m/z[M+H] calcd for C21H19N4O3: 375.1457; found: 375.1469.

Sources & evidence

ORD record
ord-b633e08447d1461b94477a6ae6091665
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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