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

HRID 552443Notes

Reaction equation

HRID 552443 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:29](Cl)(=[O:31])=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[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:29]([C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)(=[O:31])=[O:30])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 665601-Naphthalenesulfonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141108N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)naphthalene-1-sulfonamideYield 57%

Procedure

Method K was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and naphthalene-1-sulfonyl chloride to afford the title compound as a brown solid (32 mg, 57%). 1H-NMR (δ, ppm, DMSO-d6): 6.09 (d, 1H, HPy,5, J=6.0 Hz), 6.68 (m, 2H, Harom), 6.87 (d, 1H, Harom, J=8.5 Hz), 7.20 (ps t, 1H, Harom, J=8.0 Hz), 7.60 (ps t, 1H, Harom, J=7.5 Hz), 7.65-7.73 (m, 3H, Harom+Py,6), 8.08 (d, 1H, Harom, J=8.0 Hz), 8.12 (d, 1H, Harom, J=7.5 Hz), 8.23 (d, 1H, Harom, J=8.5 Hz), 8.67 (d, 1H, Harom, J=8.5 Hz), 10.83 (s, 1H, NHSO2), 11.08 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.48, 108.98, 113.81, 114.02, 114.77, 124.06, 124.40, 127.03, 127.33, 128.21, 129.13, 129.97, 130.73, 133.74, 133.92, 134.60, 139.14, 141.21, 143.88, 147.15, 154.13, 155.01. HRMS (EI): m/z [M+H] calcd for C22H17N4O4S: 433.0971; found: 433.0969.

Sources & evidence

ORD record
ord-c3fb5662bd594537934354e2ab0123dc
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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