3-Tert-pentylbenzoic acid → HCID 45141756, compound

HRID 552434

Reaction equation

HRID 552434 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:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28])([CH2:22][CH3:23])([CH3:21])[CH3:20]>>[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:27](=[O:28])[C:26]4[CH:30]=[CH:31][CH:32]=[C:24]([C:19]([CH2:22][CH3:23])([CH3:20])[CH3:21])[CH:25]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 81671153-Tert-pentylbenzoic acidHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141756HCID 45141756, compoundYield 31%

Procedure

Method H2 was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-tert-pentylbenzoic acid to afford the title compound as a light pink solid (54 mg, 31%). 1H-NMR (δ, ppm, DMSO-d6): 0.63 (t, 3H, CH3Et, J=7.4 Hz), 1.29 (s, 6H, CH3Me), 1.66 (q, 2H, CH2Et, J=7.4 Hz), 6.49 (d, 1H, HPy,5, J=5.9 Hz), 6.90 (dd, 1H, Harom, J=7.4 Hz, J=1.7 Hz), 7.41-7.47 (m, 2H, Harom), 7.56 (d, 1H, Harom, J=7.8 Hz), 7.65-7.66 (m, 2H, Harom), 7.75 (d, 1H, Harom, J=7.7 Hz) 7.81 (d, 1H, HPy,6, J=5.9 Hz), 7.84 (s, 1H, Harom), 10.30 (s, 1H, NHamide), 11.21 (s, 1H, NHurea), 11.39 (s, 1H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 8.89 (CH3Et), 28.03 (CH3), 35.90 (C(CH3)3Et,) 37.66 (CH2Et), 106.38, 110.81, 113.58, 114.28, 116.27, 124.61, 124.89, 127.91, 129.16, 129.98, 134.30, 140.76, 141.22, 144.57, 147.02, 149.24, 154.09, 154.56, 165.97. HRMS (EI): m/z [M+H] calculated for C24H24N4O3: 417.1921, found: 417.1923.

Sources & evidence

ORD record
ord-97e1a0841e0c4fb29cab7b4f7c50b2b3
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Linked notes

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