7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one → 1-[2-(4-Chlorophenyl)-5-methylpyrazol-3-yl]-3-[4-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-7-yl)oxy]phenyl]urea

HRID 1864657Notes

Reaction equation

HRID 1864657 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH:13][C:14](=[O:22])OC3C=CC=CC=3)=[CH:11][C:10]([CH3:23])=[N:9]2)=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:41]=[CH:40][C:28]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]3[NH:36][C:37](=[O:39])[NH:38][C:31]=23)=[CH:27][CH:26]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([NH:13][C:14]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([O:29][C:30]4[CH:35]=[CH:34][N:33]=[C:32]5[NH:36][C:37](=[O:39])[NH:38][C:31]=45)=[CH:40][CH:41]=3)=[O:22])=[CH:11][C:10]([CH3:23])=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 426260467-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 46196893phenyl 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl-carbamate

Product 1

HCID 461977721-[2-(4-Chlorophenyl)-5-methylpyrazol-3-yl]-3-[4-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-7-yl)oxy]phenyl]ureaYield 81.4%

Procedure

Method F was used with phenyl 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl-carbamate (41 mg, 0.12 mmol) and 7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (20 mg, 0.08 mmol). The solid residue obtained after evaporation of the solvents was washed only with Et2O to afford the title compound (31 mg, 79%) as a pale pink solid. 1H-NMR (6, ppm, DMSO-d6): 2.19 (s, 3H, CH3), 6.28 (s, 1H, HPyz,4), 6.31 (d, 1H, HPy,5, J=5.8 Hz), 7.10 (d, 2H, Harom,Ph,3+5, J=8.9 Hz), 7.47 (d, 2H, Harom,Ph,2+6, J=8.9 Hz), 7.57 (m, 4H, Harom,4—Cl—Ph), 7.74 (d, 1H, HPy,6, J=5.8 Hz), 8.47 (bs, 1H, NHurea), 9.05 (bs, 1H, NHurea), 11.19 (bs, 1H, NHPy3), 11.37 (bs, 1H, NHPy2). 13C-NMR (6, ppm, DMSO-d6): 13.7, 99.3, 105.1, 112.8, 119.8, 120.5, 125.7, 129.2, 131.5, 136.3, 137.2, 137.5, 141.2, 145.8, 146.8, 148.2, 148.5, 151.6, 154.1. LC-MS (m/z): 476 (M+H, 100). HRMS (EI): m/z [M+H]+ calcd. for C23H19N7O3Cl: 476.1238; found: 476.1213.

Workup

  1. customThe solid residue obtained
  2. customafter evaporation of the solvents
  3. washwas washed only with Et2O

Sources & evidence

ORD record
ord-45fec1ad743e42108a9de899559f6f96
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

Loading…