1-Methylpiperazine → HCID 21254935, compound

HRID 636447Notes

Reaction equation

HRID 636447 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]([CH2:28][CH3:29])=[N:19][N:20]3[C:25]([NH2:26])=[CH:24][C:23](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]([CH2:28][CH3:29])=[N:19][N:20]3[C:25]([NH2:26])=[CH:24][C:23]([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 21254940HCID 21254940, compound

Product 1

HCID 21254935HCID 21254935, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.33 ml (3 mmol) of 1-methyl-piperazine was added to a solution of 0.4 g (1.2 mmol) of 3-benzenesulphonyl-5-chloro-2-ethyl-pyrazolo[1,5-a]pyrimidin-7-ylamine in 5 ml of DMF and stirred at 90° for 1 hr. The reaction solution was evaporated and the residue was partitioned between H2O and CH2Cl2. The aqueous phase was extracted three times with 50 ml of CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (silica gel, CH2Cl2/MeOH 9:1) and crystallization from EtOH yielded 0.24 g (50%) of 3-benzenesulphonyl-2-ethyl-5-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidin-7-yl-amine as colorless crystals, m.p.>250°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between H2O 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 (silica gel, CH2Cl2/MeOH 9:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-de9bfa08e0144e49a5df9fd9e5c3efda
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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