1-Methylpiperazine → HCID 178503604, compound

HRID 636451Notes

Reaction equation

HRID 636451 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:29][CH3:30])=[N:19][N:20]3[C:25]([OH:26])=[CH:24][C:23]([CH2:27]Cl)=[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:29][CH3:30])=[N:19][N:20]3[C:25]([OH:26])=[CH:24][C:23]([CH2:27][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[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 178503603HCID 178503603, compound

Product 1

HCID 178503604HCID 178503604, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.57 ml (15.70 mml) of 1-methyl-piperazine were added to a solution of 2.9 g (7.84 mmol) of 3-benzenesulphonyl-5-chloromethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 20 ml of DMF and stirred at RT for 4 hrs. The reaction solution was evaporated and the residue was partitioned between 0.5N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 4:1) yielded 1.85 g (53%) of 3-benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol as a beige powder, m.p.>220°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between 0.5N 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

Sources & evidence

ORD record
ord-fd2369674974442490370ff3b3219305
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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