Benzenesulfonyl chloride → HCID 45140724, compound

HRID 552442Notes

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

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

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

Product 1

HCID 45140724HCID 45140724, compoundYield 50%

Procedure

Method K was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and benzenesulfonyl chloride to afford the title compound as a brown solid (25 mg, 50%). 1H-NMR (δ, ppm, DMSO-d6): ): 6.21 (s, 1H, HPy,5), 6.77 (s, 2H, Harom), 6.95 (s, 1H, Harom), 7.29 (s, 1H, Harom), 7.53-7.86 (m, 6H, Harom), 10.44 (s, 1H, NHSO2), 11.12 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.39, 110.14, 113.74, 114.64, 115.83, 126.61, 129.33, 130.82, 133.09, 139.13, 139.36, 141.25, 144.12, 147.16, 154.15, 154.97. HRMS (EI): m/z [M+H] calcd for C18H15N4O4S: 383.0814; found: 383.0815.

Sources & evidence

ORD record: ord-eb2efa18d8174447bfc3549a7310f378
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951819B2

Reaction notes

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