1-Methylpiperazine → HCID 135489408, compound

HRID 496008Notes

Reaction equation

HRID 496008 reaction equation
[CH:1]1([C:6]2[N:14]3[C:9]([C:10](=[O:28])[NH:11][C:12]([C:15]4[CH:16]=[C:17]([S:24](Cl)(=[O:26])=[O:25])[CH:18]=[CH:19][C:20]=4[O:21][CH2:22][CH3:23])=[N:13]3)=[C:8]([CH2:29][CH3:30])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:22]([O:21][C:20]1[CH:19]=[CH:18][C:17]([S:24]([N:35]2[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]2)(=[O:26])=[O:25])=[CH:16][C:15]=1[C:12]1[NH:11][C:10](=[O:28])[C:9]2=[C:8]([CH2:29][CH3:30])[N:7]=[C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:14]2[N:13]=1)[CH3:23]

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 135552958HCID 135552958, compound

Product 1

HCID 135489408HCID 135489408, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.42 g (0.92 mmol) of 3-(7-cyclopentyl-5-ethyl-4-oxo-3,4-dihydroimidazo-[5,1-f][1,2,4]triazin-2-yl)-4-ethoxybenzenesulphonyl chloride are dissolved in 15 ml of dichloromethane and cooled to 0° C. After addition of a spatula tip of 4-dimethylaminopyridine, 0.28 g (2.76 mmol) of N-methylpiperazine are added, and the reaction mixture is stirred at room temperature overnight. The mixture is diluted with dichloromethane, the organic phase is washed with ammonium chloride solution and dried over sodium sulphate and the solvent is removed under reduced pressure. Crystallization from ether gives 0.395 g (80%) of a colourless solid.

Workup

  1. additionare added
  2. washthe organic phase is washed with ammonium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed under reduced pressure
  5. customCrystallization from ether

Sources & evidence

ORD record
ord-fe7fa9fb08a94930b27f3ca0c41b0b97
Source dataset
uspto-grants-2005_09
Patent number
US06943163B2

Reaction notes

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