7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one → HCID 46197770, compound

HRID 1864655Notes

Reaction equation

HRID 1864655 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[N:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:27][C:28]1[CH:44]=[CH:43][C:31]([O:32][C:33]2[CH:38]=[CH:37][N:36]=[C:35]3[NH:39][C:40](=[O:42])[NH:41][C:34]=23)=[CH:30][CH:29]=1>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([O:32][C:33]3[CH:38]=[CH:37][N:36]=[C:35]4[NH:39][C:40](=[O:42])[NH:41][C:34]=34)=[CH:43][CH:44]=2)=[O:19])[N:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 426260467-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 46196891Phenyl 3-tert-butyl-1-(4-fluorophenyl)-1h-pyrazol-5-ylcarbamate

Product 1

HCID 46197770HCID 46197770, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Method I1. A mixture of phenyl 3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl-carbamate (66 mg, 0.18 mmol) and 7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (30 mg, 0.12 mmol) in anhydrous THF (1.5 mL) containing 4 Angstrom molecular sieves was heated at 50° C. for 14 hours. After dilution with EtOAc (10 mL) and filtration to remove the molecular sieves, the solution was washed with 0.5 M citric acid (aqueous), saturated NaHCO3 (aqueous) and brine. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure. The orange solid residue was washed with Et2O to afford the title compound (52 mg, 85%) as a slightly orange solid. 1H-NMR (6, ppm, DMSO-d6): 1.28 (s, 9H, t-Bu), 6.31 (d, 1H, HPy,5, J=6.0 Hz), 6.35 (s, 1H, HPyz,4), 7.09 (d, 2H, Harom,Ph,3+5, J=8.9 Hz), 7.37 (t, 2H, Harom,4-F-Ph,3+5 J=8.8 Hz), 7.47 (d, 2H, Harom,Ph,2+6, J=8.9 Hz), 7.57 (dd, 2H, Harom,4-F-Ph,2+6 J=8.8 Hz and J=5.0 Hz), 7.74 (d, 1H, HPy,6, J=6.0 Hz), 8.37 (bs, 1H, NHurea), 9.06 (bs, 1H, NHurea), 11.16 (bs, 1H, NHPy3) 11.34 (bs, 1H, NHPy2). LC-MS (m/z): 502 (M+H, 100).

Workup

  1. additioncontaining 4 Angstrom molecular sieves
  2. filtrationAfter dilution with EtOAc (10 mL) and filtration
  3. customto remove the molecular sieves
  4. washthe solution was washed with 0.5 M citric acid (aqueous), saturated NaHCO3 (aqueous) and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was evaporated under reduced pressure
  7. washThe orange solid residue was washed with Et2O

Sources & evidence

ORD record
ord-422dd8ce808f4c4ca5a5f0d000313074
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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