rel-(2R,6S)-2,6-dimethylpiperazine → HCID 70000221, compound

HRID 636391Notes

Reaction equation

HRID 636391 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.[C:9]1([S:15]([C:18]2[C:19]([S:29][CH3:30])=[N:20][N:21]3[C:26](Cl)=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[C:9]1([S:15]([C:18]2[C:19]([S:29][CH3:30])=[N:20][N:21]3[C:26]([N:6]4[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]4)=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 70000221HCID 70000221, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.28 g (2 mmol) of cis-2,6-dimethylpiperazine was added to a solution of 0.35 g (1 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 5 ml of DMF and stirred at 60° for 2 hrs. The reaction solution was cooled to RT and evaporated in a high vacuum. The residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2,and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 19:1) and crystallization from EtOH yielded 0.29 g (67%) of (3R,5S)-3-benzenesulphonyl-7-(3,5-dimethyl-piperazin-1-yl)-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as colorless crystals, m.p. 220-221°.

Workup

  1. customevaporated in a high vacuum
  2. customThe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2,and the combined organic phases
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 19:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-b361592b6171498b8859d07d1bdfe042
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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