1-Methylpiperazine → HCID 21254963, compound

HRID 636442Notes

Reaction equation

HRID 636442 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: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]([S: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 21255038HCID 21255038, compound

Product 1

HCID 21254963HCID 21254963, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.1 g (1 mmol) of 1-methyl-piperazine was added to a solution of 0.14 g (0.4 mmol) of 3-benzenesulphonyl-5-chloro-2-methylsulphanyl-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 0.1 g (59%) of 3-benzenesulphonyl-5-(4-methyl-piperazin-1-yl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine as colorless crystals, m.p.>230°.

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-027dd671a9ac4395bfc2c8eaafa1b8d4
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

Loading…