HCID 21255002, compound → HCID 21254981, compound

HRID 636443Notes

Reaction equation

HRID 636443 reaction equation
[C:1]1([S:7]([C:10]2[C:11]([CH2:27][CH3:28])=[N:12][N:13]3[C:18]([N:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[CH:17][C:16](Cl)=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[Pd]>[C:1]1([S:7]([C:10]2[C:11]([CH2:27][CH3:28])=[N:12][N:13]3[C:18]([N:19]4[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]4)=[CH:17][CH:16]=[N:15][C:14]=23)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 21255002HCID 21255002, compound

Product 1

HCID 21254981HCID 21254981, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.1 g of Pd/C (10%) was added to a solution of 0.267 g (0.63 mmol) of 3-benzenesulphonyl-5-chloro-2-ethyl-7-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidine in 40 ml of EtOH and the mixture was hydrogenated at RT for 4 hrs. The reaction mixture was filtered over Dicalite and the filtrate was evaporated. The residue was partitioned between CH2Cl2 and sat. NaHCO3 solution. The aqueous phase was extracted three times with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography of the residue (SiO2CH2Cl2/MeOH 19:1) and crystallization from EtOH yielded 0.2 g (53%) of as pale beige crystals, m.p. 206-207°.

Workup

  1. filtrationThe reaction mixture was filtered over Dicalite
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between CH2Cl2 and sat. NaHCO3 solution
  4. extractionThe aqueous phase was extracted three times with CH2Cl2
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customChromatography of the residue (SiO2CH2Cl2/MeOH 19:1) and crystallization from EtOH
  9. customyielded 0.2 g (53%) of as pale beige crystals, m.p. 206-207°

Sources & evidence

ORD record
ord-b71485b59c6d4c16b443edecf1ba5f2c
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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