2-Methoxyethylamine → 4-Ethoxy-N-(2-methoxy-ethyl)-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonamide

HRID 8627

Reaction equation

HRID 8627 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][C:10]=1[C:19]1[NH:24][C:23](=[O:25])[N:22]2[C:26]([CH3:32])=[N:27][C:28]([CH2:29][CH2:30][CH3:31])=[C:21]2[N:20]=1)[CH3:7]>ClCCl>[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:17])=[O:16])=[CH:11][C:10]=1[C:19]1[NH:24][C:23](=[O:25])[N:22]2[C:26]([CH3:32])=[N:27][C:28]([CH2:29][CH2:30][CH3:31])=[C:21]2[N:20]=1)[CH3:7]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 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 1357235124-Ethoxy-N-(2-methoxy-ethyl)-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

55 mg (0.73 mmol) of 2-methoxyethylamine 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-a][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) and stirring up with diethyl ether, 64 mg (57%) of 4-ethoxy-N-(2-methoxy-ethyl)-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonamide are obtained.

Workup

  1. customAfter chromatographic purification (dichloromethane/methanol=95:5)
  2. stirringstirring up with diethyl ether, 64 mg (57%) of 4-ethoxy-N-(2-methoxy-ethyl)-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonamide
  3. customare obtained

Sources & evidence

ORD record
ord-0dfab5ad94fb4f82b5caaa410a7bfb95
Source dataset
uspto-grants-2006_08
Patent number
US07091203B2

Linked notes

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