1-Methylpiperazine → HCID 21254914, compound

HRID 636432Notes

Reaction equation

HRID 636432 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]1([S:14]([C:17]2[C:18]([S:31][CH3:32])=[N:19][N:20]3[C:25](Cl)=[CH:24][C:23]([CH2:27][CH2:28][O:29][CH3:30])=[N:22][C:21]=23)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C=O)C>[C:8]1([S:14]([C:17]2[C:18]([S:31][CH3:32])=[N:19][N:20]3[C:25]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:24][C:23]([CH2:27][CH2:28][O:29][CH3:30])=[N:22][C:21]=23)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 21255049HCID 21255049, compound

Product 1

HCID 21254914HCID 21254914, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.5 g (5 mmol) of 1-methyl-piperazine in 3 ml of DMF was added to a solution of 0.45 g (1.13 mmol) of 3-benzenesulphonyl-7-chloro-5-(2-methoxy-ethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 20 ml of DMF and stirred at RT for 3 hrs. The reaction solution was evaporated, the residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2, the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (silica gel, CH2Cl2/MeOH 12:1) and crystallization from EtOH yielded 0.255 g (67%) of 3-benzenesulphonyl-5-(2-methoxy-ethyl)-7-(4-methyl-piperazin-1-yl)-2-methylsulphanyl-pyrazolo[1,5-a]-pyrimidine as colorless crystals, m.p. 160-161°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (silica gel, CH2Cl2/MeOH 12:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-5207724e7a934a0983479ef0d10e5be5
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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