HCID 17750736, compound → HCID 45141564, compound

HRID 552428Notes

Reaction equation

HRID 552428 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:33])([F:32])[O:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([Cl:31])[CH:30]=1)[C:25](Cl)=[O:26]>>[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:25](=[O:26])[C:24]4[CH:28]=[C:29]([Cl:31])[CH:30]=[C:22]([O:21][C:20]([F:33])([F:19])[F:32])[CH:23]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 17750736HCID 17750736, compoundHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141564HCID 45141564, compoundYield 38.9%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]-pyridin-2(3H)-one and 3-trifluoromethoxy-5-chlorobenzoyl chloride to afford the title compound (38 mg, 38.9%). 1H-NMR (δ, ppm, DMSO-d6): 6.49 (d, 1H, HPy,5, J=5.9 Hz), 6.93-6.96 (m, 1H, Harom), 7.44 (t, 1H, Harom-5, J=8.0 Hz), 7.58 (s, 1H, Harom-2), 7.63-7.65 (m, 1H, Harom), 7.81 (d, 1H, HPy,6, J=5.9 Hz), 7.82 (m, 1H, Harom′), 7.86 (m, 1H, Harom′), 8.08 (t, 1H, Harom′, J=1.6 Hz), 10.53 (s, 1H, NHamide), 11.20 (s, 1H, NHPy7), 11.40 (s, 1H, NHPy9). LC-MS, tR=5.13 minutes, m/z: 467.05 (M+H)+, calculated for C20H13N4O4F3Cl. HRMS (EI): m/z [M+H] calculated for C20H13N4O4F3Cl: 465.0585; found: 465.0583.

Sources & evidence

ORD record
ord-3f32e16b9197400ebfe69e2568a183e7
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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