Dichloromethane → 3-Cyclohexyl-6-{2-methoxy-4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl}-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 915934Notes

Reaction equation

HRID 915934 reaction equation
ClCCl.[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][C:21]=4[O:30][CH3:31])=[N:14][C:13]=3[N:12]([CH3:32])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(N(CC)CC)C>O>[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([N:37]5[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]5)(=[O:28])=[O:27])=[CH:22][C:21]=4[O:30][CH3:31])=[N:14][C:13]=3[N:12]([CH3:32])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 1360059474-(3-Cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxybenzenesulfonyl chloride

Product 1

HCID 1360057943-Cyclohexyl-6-{2-methoxy-4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl}-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2 ml anhydrous dichloromethane solution of 87.2 mg (0.2 mmol) of the compound obtained in Example 48, 26.6 μl (0.24 mmol) of N-methylpiperazine and 70 μl (0.5 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 20 hours. Then, water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1˜30/1) to obtain 87 mg (87%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1˜30/1)

Sources & evidence

ORD record
ord-50bf40bbffae4bb5808c2d6a88d27d24
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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