7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one → HCID 45141329, compound

HRID 552425Notes

Reaction equation

HRID 552425 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]([CH2:28][C:29](Cl)=[O:30])[CH:25]=[CH:26][CH:27]=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][C:29](=[O:30])[CH2:28][C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([O:21][C:20]([F:32])([F:19])[F:33])[CH:23]=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 86102346HCID 86102346, compound

Product 1

HCID 45141329HCID 45141329, compoundYield 23.5%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]-pyridin-2(3H)-one and 2-(3-trifluoromethoxyphenyl)-acetyl chloride to afford the title compound (22 mg, 23.5%). 1H-NMR (δ, ppm, DMSO-d6): 3.71 (s, 2H, CH2), 6.43 (d, 1H, HPy,5, J=5.9 Hz), 6.83-6.86 (m, 1H, Harom), 7.24-7.47 (m, 8H, Harom), 7.78 (d, 1H, HPy,6, J=5.9 Hz), 10.37 (s, 1H, NHamide), 11.21 (s, 1H, NHPy7), 11.42 (s, 1H, NHPy9). LC-MS, tR=4.65 minutes, m/z: 445.04 (M+H)+, calculated for C21H16N4O4F3. HRMS (EI): m/z [M+H] calculated for C21H16N4O4F3: 445.1124; found: 445.1107.

Sources & evidence

ORD record
ord-fc2f5e4c2b824608a5a37dac9d1f7c30
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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