Ethanol → N-(6-Methanesulphonamido-2-quinolylmethyl)-N-methyl-4-methanesulphonamidophenethylamine
Reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=2)[N:4]=1.[CH2:18](O)[CH3:19]>>[CH3:17][S:14]([NH:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[C:3]([CH2:2][N:4]([CH2:3][CH2:2][C:19]1[CH:18]=[CH:9][C:8]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:7][CH:6]=1)[CH3:5])[CH:12]=[CH:11]2)(=[O:16])=[O:15]Participants
Procedure
4-[2-(Methylamino)ethyl]methanesulphonanilide (0.228 g, 1 mmol--see Preparation 14(B)) and 2-chloromethyl-6-methanesulphonamidoquinoline (0.135 g, 0.5 mmol--see Preparation 12(D)) were heated in ethanol solution (5 ml) at reflux for 4 hours. The solvent was then evaporated in vacuo and the residue dissolved in methylene chloride, washed with water, dried (MgSO4), filtered and evaporated in vacuo. The resulting gum was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated in vacuo to give a foam which crystallised from ethanol, yield of the title compound 0.45 g, m.p. 165°-166°, confirmed spectroscopically to be identical to the product of Example 5.
Workup
- temperatureat reflux for 4 hours
- customThe solvent was then evaporated in vacuo
- dissolutionthe residue dissolved in methylene chloride
- washwashed with water
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated in vacuo
- customThe resulting gum was purified by column chromatography on silica eluting with methylene chloride
- additioncontaining methanol (0% up to 1%)
- customevaporated in vacuo
- customto give a foam which
- customcrystallised from ethanol, yield of the title compound 0.45 g, m.p. 165°-166°
Sources & evidence
- ORD record
- ord-f6e2e1a2fd424c3ba325b18ff7fb0eef
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04956382
Reaction notes
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