3-Chloropropanesulphonyl chloride → HCID 136005954, compound

HRID 915967Notes

Reaction equation

HRID 915967 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][N:14]([CH3:23])[C:12]=3[N:13]=2)=[C:4]([O:25][CH3:26])[CH:3]=1.Cl[CH2:28][CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH:17]1([C:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:1]5[CH2:28][CH2:29][CH2:30][S:31]5(=[O:33])=[O:32])=[CH:3][C:4]=4[O:25][CH3:26])=[N:13][C:12]=3[N:14]([CH3:23])[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 154103-Chloropropanesulphonyl chlorideHCID 516892Sodium BicarbonateHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 136005954HCID 136005954, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 2 ml pyridine solution of 100 mg (0.280 mmol) of the compound obtained in Example 44, 85.2 μl (0.700 mmol) of 3-chloropropanesulfonyl chloride was added, and the mixture was stirred at room temperature for 8 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. To the residue, 2 ml of ethanol and a 1M aqueous solution of sodium hydroxide were added, and the mixture was stirred at room temperature for 48 hours. Then, the reaction mixture was neutralized with a 1M aqueous solution of hydrochloric acid, and extracted with ethyl acetate. 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 (ethyl acetate) to obtain 68 mg (53%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. additionTo the residue, 2 ml of ethanol and a 1M aqueous solution of sodium hydroxide were added
  6. stirringthe mixture was stirred at room temperature for 48 hours
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3070a5728a054da6a00663a05eb710fe
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

Loading…