m-Anisoyl chloride → HCID 58024296, compound

HRID 552408Notes

Reaction equation

HRID 552408 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.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[NH:12][C:13](=[O:15])[NH:14][C:7]=23)[CH:3]=1)=[O:25]

Participants

3

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 58024296HCID 58024296, compoundYield 40%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-methoxy-benzoyl chloride to afford the title compound as a brown solid (21 mg, 40%). 1H-NMR (δ, ppm, DMSO-d6): 3.83 (s, 3H, OMe), 6.49 (d, 1H, HPy,5, J=5.8 Hz), 6.90 (d, 1H, Harom, J=7.48 Hz), 7.16 (d, 1H, Harom, J=6.52 Hz), 7.39-7.49 (m, 3H, Harom), 7.52 (d, 1H, Harom, J=7.61 Hz), 7.62-7.68 (m, 2H, Harom), 7.81 (d, 1H, HPy,6, J=5.44 Hz), 10.31 (s, 1H, NHamide), 11.19 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2).

Sources & evidence

ORD record
ord-d4814be2465d4e648aa476cb94f7931e
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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