Ammonium Chloride → 4-methoxy-3-[4-(4-morpholinyl)phenyl]-1H-Pyrazolo[4,3-c]pyridine

HRID 2206244Notes

Reaction equation

HRID 2206244 reaction equation
C([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[C:10]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[N:9]1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O.C1COCC1>[CH3:18][O:17][C:12]1[C:11]2[C:10]([C:19]3[CH:20]=[CH:21][C:22]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:23][CH:24]=3)=[N:9][NH:8][C:16]=2[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 1179878001-benzyl-4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1179878324-methoxy-3-[4-(4-morpholinyl)phenyl]-1H-Pyrazolo[4,3-c]pyridineYield 70.2%

Reagents, catalysts & solvents 1

HCID 21830753dimethylsulfoxide THFSolvent

Procedure

To a solution of 1-benzyl-4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (0.68 g) in DMSO/THF (10 mL/2.5 mL) was added potassium tert-butoxide (1.90 g) under ice-cooling. The reaction mixture was stirred at room temperature for 5 hr. The reaction mixture was added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (0.37 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-3a286283f627421aa5ff64ceca025aff
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…