N-Methylhomoveratrylamine → N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-4-ethoxy-N-methyl-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzenesulfonamide

HRID 8626

Reaction equation

HRID 8626 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][C:19]=1[C:28]1[NH:33][C:32](=[O:34])[N:31]2[C:35]([CH3:41])=[N:36][C:37]([CH2:38][CH2:39][CH3:40])=[C:30]2[N:29]=1)[CH3:16]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:14])[S:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:15][CH3:16])=[C:19]([C:28]3[NH:33][C:32](=[O:34])[N:31]4[C:35]([CH3:41])=[N:36][C:37]([CH2:38][CH2:39][CH3:40])=[C:30]4[N:29]=3)[CH:20]=2)(=[O:25])=[O:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 77039N-MethylhomoveratrylamineHCID 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 135723511N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-4-ethoxy-N-methyl-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

143 mg (0.73 mmol) of N-(3,4-dimethoxyphenylethyl)-N-methylamine 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), 138 mg (98%) of N-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-ethoxy-N-methyl-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzene-sulfonamide are obtained.

Workup

  1. customAfter chromatographic purification (dichloromethane/methanol=95:5), 138 mg (98%) of N-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-ethoxy-N-methyl-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzene-sulfonamide
  2. customare obtained

Sources & evidence

ORD record
ord-936d5bb6add248b09e6db41a86e6f77c
Source dataset
uspto-grants-2006_08
Patent number
US07091203B2

Linked notes

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