7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one → HCID 45140727, compound

HRID 552406Notes

Reaction equation

HRID 552406 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]1[CH:21]=[C:22]([CH:26]=[C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:28]=1)[C:23](Cl)=[O:24]>>[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:28]=1)[C:23]([NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[NH:12][C:13](=[O:15])[NH:14][C:7]=23)[CH:3]=1)=[O:24]

Participants

3

Reactant 2

HCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 86238504HCID 86238504, compound

Product 1

HCID 45140727HCID 45140727, compoundYield 65%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-fluoro-5-morpholinobenzoyl chloride to afford the title compound as a light brown solid (38 mg, 65%). 1H-NMR (δ, ppm, DMSO-d6): 3.22 (m, 4H, CH2N), 3.74 (m, 4H, CH2O), 6.48 (d, 1H, HPy,5, J=6.0 Hz), 6.91 (d, 1H, Harom, J=8.0 Hz), 6.98 (d, 1H, Harom, J=10.5 Hz), 7.11 (d, 1H, Harom, J=9.0 Hz), 7.26 (s, 1H, Harom,Ph′), 7.42 (ps t, 1H, Harom, J=8.5 Hz), 7.61-7.64 (m, 2H, Harom), 7.81 (d, 2H, HPy,6, J=6.0 Hz), 10.28 (s, 1H, NHamide), 11.19 (s, 1H, NHPy3), 11.38 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 47.76, 65.85, 104.17, 104.41, 106.58, 109.73, 110.86, 113.75, 114.57, 116.35, 130.16, 137.05, 140.61, 141.35, 144.60, 147.15, 152.65, 154.21, 154.73, 162.98, 164.81. HRMS (EI): m/z [M+H] calcd for C23H21FN5O4: 450.1578; found: 450.1571.

Sources & evidence

ORD record
ord-b16ed0d23a994087b6144a43871eedfa
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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