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 278860Notes

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]

Participants

Conditions

Temperature: 0 °C

Procedure

0.1 g (0.26 mmol) of 4-ethoxy-3-(5,7-dimethyl4-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

additionare added
washthe organic phase is washed with ammonium chloride solution
dry with materialdried over sodium sulphate
customthe solvent is removed under reduced pressure
customThe residue is chromatographed over silica gel (dichloromethane/methanol 9:1)

Sources & evidence

ORD record: ord-21bad19d28f541ff9f406fbdf28625a4
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362178B1

Reaction notes

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