Hydrochloric Acid → 4-(3-Cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxybenzenesulfonyl chloride

HRID 915933Notes

Reaction equation

HRID 915933 reaction equation
[ClH:1].N[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11](=[O:25])[C:12]3[C:17]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:16][N:15]([CH3:24])[C:13]=3[N:14]=2)=[C:5]([O:26][CH3:27])[CH:4]=1.N([O-])=O.[Na+].[S:32](=[O:34])=[O:33]>O.[Cu](Cl)Cl.C(O)(=O)C>[CH:18]1([C:17]2[C:12]3[C:11](=[O:25])[NH:10][C:9]([C:6]4[CH:7]=[CH:8][C:3]([S:32]([Cl:1])(=[O:34])=[O:33])=[CH:4][C:5]=4[O:26][CH3:27])=[N:14][C:13]=3[N:15]([CH3:24])[N:16]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 23668193Sodium NitriteHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 1360059474-(3-Cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxybenzenesulfonyl chlorideYield 73%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a 2.5 ml concentrated hydrochloric acid/8.5 ml acetic acid mixed solution of 750 mg (2.12 mmol) of the compound obtained in Example 44, a solution of 220 mg (3.2 mmol) of sodium nitrite in 1.5 ml of water was added with ice cooling. The mixture was stirred for 30 minutes at the same temperature. To the resulting solution, 87 mg (0.65 mmol) of copper dichloride and 4.5 ml of a 22% acetic acid solution of sulfur dioxide were added, and the mixture was stirred at room temperature for 6 hours. Then, water was added to the reaction mixture, and precipitated solids were collected by filtration. The collected solids were dissolved in dichloromethane again, and the solution was washed with water and a saturated aqueous solution of sodium chloride. The washed solution was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Ether was added to the residue, and the cake was collected by filtration to obtain 673 mg (73%) of the captioned compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. customprecipitated solids
  3. filtrationwere collected by filtration
  4. dissolutionThe collected solids were dissolved in dichloromethane again
  5. washthe solution was washed with water
  6. dry with materialThe washed solution was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionEther was added to the residue
  9. filtrationthe cake was collected by filtration

Sources & evidence

ORD record
ord-5289208f305444c9bbcd9470842bee47
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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