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1-Methylpiperazine → 2-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-5,7-dimethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 645435
Notes
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Reaction equation

HRID 645435 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]2=[C:21]([CH3:25])[N:22]=[C:23]([CH3:24])[N:16]2[N:15]=1)[CH3:2].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:30]2[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]2=[C:21]([CH3:25])[N:22]=[C:23]([CH3:24])[N:16]2[N:15]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 1358567774-Ethoxy-3-(5,7-dimethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride

Product 1

HCID 1355155752-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-5,7-dimethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

0.1 g (0.26 mmol) of 4-ethoxy-3-(5,7-dimethyl-4-oxo-3,4-dihydroimidazo-[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride are dissolved in 10 ml of dichloromethane and cooled to 0° C. After addition of a spatula tip of DMAP, 80 mg (0.784 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. The residue is chromatographed over silica gel (dichloromethane/methanol 9:1).

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. customThe residue is chromatographed over silica gel (dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-14690a0c004c447aa6e85185120bc909
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07704999B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes