Piperazine → HCID 21254934, compound

HRID 636415Notes

Reaction equation

HRID 636415 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([S:13]([C:16]2[C:17]([CH2:27][CH3:28])=[N:18][N:19]3[C:24](Cl)=[CH:23][C:22]([CH3:26])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[C:7]1([S:13]([C:16]2[C:17]([CH2:27][CH3:28])=[N:18][N:19]3[C:24]([N:1]4[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]4)=[CH:23][C:22]([CH3:26])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 21255014HCID 21255014, compound

Product 1

HCID 21254934HCID 21254934, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.64 g (7.4 mmol) of piperazine in 10 ml of DMF was added to a solution of 1.0 g (3 mmol) of 3-benzenesulphonyl-7-chloro-2-ethyl-5-methyl-pyrazolo[1,5-a]pyrimidine in 10 ml of DMF and stirred at 60° for 2 hrs. The DMF was evaporated in a high vacuum, the residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with 50 ml of CH2Cl2 and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 9:1) and crystallization from EtOH yielded 0.32 g (27%) of 3-benzenesulphonyl-2-ethyl-5-methyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine as colorless crystals, m.p. 150-150.8°.

Workup

  1. customThe DMF was evaporated in a high vacuum
  2. customthe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with 50 ml of CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 9:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-67facba39b0544efa7788c67a8d33dd3
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

Loading…