3-tert-Butylbenzoyl chloride → 3-Tert-butyl-N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)benzamide

HRID 552432Notes

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.[C:19]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([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:27])([CH3:22])([CH3:20])[CH3:21]

Participants

Reactant 2

HCID 221431023-tert-Butylbenzoyl chloride

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

Product 1

HCID 451417553-Tert-butyl-N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)benzamideYield 54%

Procedure

Method H was used Method H was used with 7-(3-Aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-tert-butylbenzoyl chloride to afford the title compound as a light pink solid (90 mg, 54%). 1H-NMR (δ, ppm, DMSO-d6): 1.32 (s, 9H, tBu), 6.49 (d, 1H, HPy,5, J=5.9 Hz), 6.91 (d, 1H, Harom, J=6.7 Hz), 7.41-7.46 (m, 2H, Harom), 7.62-7.66 (m, 3H, Harom), 7.75 (d, 1H, Harom, J=7.6 Hz), 7.81 (d, 1H, HPy,6, J=5.9 Hz), 7.89 (s, 1H, Harom,), 10.35 (s, 1H, NHamide), 11.26 (s, 1H, NHurea), 11.44 (s, 1H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 30.98 (C(CH3)3), 34.55 (C(CH3)3), 106.41, 110.83, 113.60, 114.40, 116.31, 124.30, 124.78, 128.09, 128.67, 130.11, 134.42, 140.84, 141.31, 144.67, 147.06, 150.90, 154.17, 154.58, 166.06. HRMS (EI): m/z [M+H] calculated for C23H22N4O3: 403.1765; found: 403.1762.

Sources & evidence

ORD record: ord-acb2f32996064c0fadcd818c714b090e
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951819B2

Reaction notes

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