4-Chlorobenzoyl chloride → HCID 45141326, compound

HRID 552421Notes

Reaction equation

HRID 552421 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.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:1][C:2]2[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]3[CH:11]=[CH:10][N:9]=[C:8]4[NH:12][C:13](=[O:15])[NH:14][C:7]=34)[CH:3]=2)=[O:25])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141326HCID 45141326, compoundYield 15%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 4-chlorobenzoyl chloride to afford the title compound (11 mg, 15%). 1H-NMR (δ, ppm, DMSO-d6): 6.49 (d, 1H, HPy,5, J=6.0 Hz), 6.91 (d, 1H, Harom, J=8.0 Hz), 7.42 (t, 1H, Harom, J=8.0 Hz), 7.59-7.63 (m, 3H, Harom), 7.65 (d, 1H, Harom, J=8.0 Hz), 7.80 (d, 1H, HPy,6, J=6.0 Hz), 7.96 (d, 2H, Harom, J=9.0 Hz), 10.40 (s, 1H, NHamide), 11.19 (s, 1H, NHPy3), 11.38 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C19H14N4O3Cl: 381.0754; found: 381.0753.

Sources & evidence

ORD record
ord-bc0d4b14abab4bec8aaa8bccbc86d0cb
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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