Dimethyl Sulfoxide → 2-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexanone

HRID 2206267Notes

Reaction equation

HRID 2206267 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[C:18]2[C:19]([C:29]3[CH:34]=[CH:33][C:32]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[CH:31][CH:30]=3)=[N:20][N:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]3[OH:28])[C:17]=2[CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>ClCCl>[CH3:11][O:12][C:13]1[C:18]2[C:19]([C:29]3[CH:34]=[CH:33][C:32]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[CH:31][CH:30]=3)=[N:20][N:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])[C:17]=2[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1179877732-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexanol

Product 1

HCID 1179881552-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexanoneYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (910 mg) in dichloromethane (3 mL) was added DMSO (670 mg) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 30 min, and a solution of 2-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexanol (350 mg) in dichloromethane (2 mL) was added thereto. The reaction mixture was stirred at −78° C. for 1 hr, and triethylamine (1.2 g) was added thereto. The reaction mixture was stirred at −78° C. for 1.5 hr, and added to ice-water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate solution, 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 (190 mg).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 1 hr
  2. stirringThe reaction mixture was stirred at −78° C. for 1.5 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-7fd30b7be7554a05bc2b9a813d7feae6
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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