3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 45140534, compound

HRID 552441Notes

Reaction equation

HRID 552441 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.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=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:27]([C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:19])([F:31])[F:32])[CH:22]=4)(=[O:29])=[O:28])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45140534HCID 45140534, compoundYield 72%

Procedure

Method K was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-(trifluoromethyl)benzenesulfonyl chloride to afford the title compound as an off-white solid (42 mg, 72%). 1H-NMR (δ, ppm, DMSO-d6): 6.19 (d, 1H, HPy,5, J=5.5 Hz), 6.78 (s, 1H, Harom), 6.86 (d, 1H, Harom, J=8.0 Hz), 6.98 (d, 1H, Harom, J=7.5 Hz), 7.31-7.35 (m, 1H, Harom), 7.74 (d, 1H, HPy,6, J=5.5 Hz), 7.82-7.85 (m, 1H, Harom), 7.96-8.06 (m, 4H, Harom), 10.57 (s, 1H, NHSO2), 11.13 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.21, 110.98, 113.74, 115.45, 116.59, 123.09, 123.24, 129.88, 130.68, 131.02, 131.08, 138.71, 138.72, 140.20, 141.16, 144.09, 147.21, 154.15, 155.04. HRMS (EI): m/z [M+H] calcd for C19H14F3N4O4S: 451.0688; found: 451.0687.

Sources & evidence

ORD record
ord-8c64005cb4bb4187b23db29b7784d256
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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