Chlorosulfonic acid → HCID 135430979, compound

HRID 2186762Notes

Reaction equation

HRID 2186762 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH2:23][CH2:24][CH3:25])[NH:13][C:14](=[O:15])[C:9]=3[C:8]([CH2:26][CH3:27])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[S:29]([OH:32])(=O)=[O:30].[CH2:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH3:34].S(Cl)(Cl)(=O)=O>ClCCl>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C:16]4[CH:21]=[C:20]([S:29]([N:38]5[CH2:39][CH2:40][N:35]([CH2:33][CH3:34])[CH2:36][CH2:37]5)(=[O:32])=[O:30])[CH:19]=[CH:18][C:17]=4[O:22][CH2:23][CH2:24][CH3:25])[NH:13][C:14](=[O:15])[C:9]=3[C:8]([CH2:26][CH3:27])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 24638Chlorosulfonic acidHCID 24648Sulfuryl chlorideHCID 791961-EthylpiperazineHCID 135484584HCID 135484584, compound

Product 1

HCID 135430979HCID 135430979, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-Cyclopentyl-3-ethyl-6-(2-n-propoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (WO 96/28448) (500 mg, 1.36 mmol) was added portionwise to chlorosulphonic acid (1.6 g, 13.6 mmol) and the reaction stirred at room temperature for 18 hours. The reaction was poured into a mixture of ice water (30 ml) and dichloromethane (30 ml) with stirring, the layers separated and the aqueous extracted with dichloromethane (2×30 ml). The combined organic solutions were washed with brine (30 ml), dried (Na2SO4) and evaporated under reduced pressure, to give a foam. N-Ethylpiperazine (108 mg, 0.95 mmol) was added dropwise to an ice-cold solution of this intermediate sulphonyl chloride in dichloromethane (3 ml) and the reaction stirred at room temperature for 2 hours. The mixture was diluted with dichloromethane (10 ml), washed consecutively with water (5 ml), saturated sodium bicarbonate solution (5 ml) and brine (5 ml), dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 96:4) to afford the title compound, (81 mg).

Workup

  1. stirringwith stirring
  2. customthe layers separated
  3. extractionthe aqueous extracted with dichloromethane (2×30 ml)
  4. washThe combined organic solutions were washed with brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give a foam
  8. stirringthe reaction stirred at room temperature for 2 hours
  9. washwashed consecutively with water (5 ml), saturated sodium bicarbonate solution (5 ml) and brine (5 ml)
  10. dry with materialdried (Na2SO4)
  11. customevaporated under reduced pressure
  12. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4ea21de091bd4af5aec929b5608ac317
Source dataset
uspto-grants-2002_06
Patent number
US06407114B1

Reaction notes

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