1-Ethylpiperazine → 2-[2-Ethoxy-5-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-6-methyl-8-propyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one

HRID 392667

Reaction equation

HRID 392667 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][C:13]=1[C:22]1[NH:27][C:26](=[O:28])[N:25]2[C:29]([CH3:35])=[N:30][C:31]([CH2:32][CH2:33][CH3:34])=[C:24]2[N:23]=1)[CH3:10]>ClCCl>[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)(=[O:20])=[O:19])=[CH:14][C:13]=1[C:22]1[NH:27][C:26](=[O:28])[N:25]2[C:29]([CH3:35])=[N:30][C:31]([CH2:32][CH2:33][CH3:34])=[C:24]2[N:23]=1)[CH3:10]

Participants

4

Reactant 2

HCID 791961-EthylpiperazineHCID 1354246684-Ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzene-sulfonyl chloride

Product 1

HCID 1355305762-[2-Ethoxy-5-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-6-methyl-8-propyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

83 mg (0.73 mmol) of N-ethylpiperazine are added to a solution of 100 mg (0.24 mmol) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-α]-[1,3,5]triazin-2-yl)-benzenesulfonyl chloride (example VI) in 5 ml of dichloromethane and the reaction mixture is stirred at room temperature for 2 hours. After chromatographic purification (dichloromethane/methanol=95:5), 104 mg (87%) of 2-[2-ethoxy-5-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-6-methyl-8-propyl-3H-imidazo[1,5-α][1,3,5]triazin-4-one are obtained.

Workup

  1. customAfter chromatographic purification (dichloromethane/methanol=95:5), 104 mg (87%) of 2-[2-ethoxy-5-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-6-methyl-8-propyl-3H-imidazo[1,5-α][1,3,5]triazin-4-one
  2. customare obtained

Sources & evidence

ORD record
ord-18689dc034ce4df0966e895fa94b966b
Source dataset
uspto-grants-2004_10
Patent number
US06803365B2

Linked notes

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