7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one → HCID 86637551, compound

HRID 552429Notes

Reaction equation

HRID 552429 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:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[S:25]>>[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][C:24](=[S:25])[C:23]4[CH:27]=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 536799043-Trifluoromethylthio-benzoyl chloride

Product 1

HCID 86637551HCID 86637551, compoundYield 17%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-trifluoromethylthio-benzoyl chloride to afford the title compound (16 mg, 17.0%). 1H-NMR (δ, ppm, DMSO-d6): 6.49 (d, 1H, HPy,5, J=5.9 Hz), 6.93 (ddd, 1H, Harom, J=0.6 Hz, J=2.4 Hz, J=8.2 Hz), 7.44 (t, 1H, Harom, J=8.2 Hz), 7.62 (t, 1H, Harom, J=2.1 Hz), 7.66 (dd, 1H, Harom, J=1.1 Hz, J=8.2 Hz), 7.71 (t, 1H, Harom, J=7.8 Hz), 7.81 (d, 1H, HPy,6, J=5.9 Hz), 7.94 (d, 1H, Harom, J=7.8 Hz), 8.16 (m, 1H, Harom), 8.26 (s, 1H, Harom), 10.50 (s, 1H, NHamide), 11.19 (s, 1H, NHPy7), 11.39 (s, 1H, NHPy9). LC-MS, tR=4.87 minutes, m/z: 447.07 (M+H)+, calculated for C20H14N4O3SF3. HRMS (EI): m/z [M+H] calculated for C20H14N4O3SF3: 447.0739; found: 447.0743.

Sources & evidence

ORD record
ord-e1a7735076d3455cb3215930588be60e
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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