Sodium Bicarbonate → 5-Methanesulphonamido-2-[N-(6-methanesulphonamidoquinol-2-ylmethyl)-N-methylamino]indane

HRID 1761867Notes

Reaction equation

HRID 1761867 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([NH:15][CH3:16])[CH2:9]2)(=[O:4])=[O:3].Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=2)[N:20]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([N:15]([CH2:18][C:19]1[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=3)[N:20]=1)[CH3:16])[CH2:9]2)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 190455722-Chloromethyl-6-methanesulphonamidoquinolineHCID 198886595-Methanesulphonamido-2-methylaminoindane

Product 1

HCID 198886585-Methanesulphonamido-2-[N-(6-methanesulphonamidoquinol-2-ylmethyl)-N-methylamino]indane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Methanesulphonamido-2-methylaminoindane (0.09 g), 2-chloromethyl-6-methanesulphonamidoquinoline (0.1 g) and sodium bicarbonate (0.2 g) were heated under reflux in acetonitrile (10 ml) for 11/2 hours. The solvent was then removed by evaporation in vacuo and the residue was taken up in methylene chloride, washed with aqueous sodium bicarbonate, dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 2%) and the product-containing fractions were combined and evaporated to give the title compound as a form, yield 0.09 g. A sample was crystallised from deuterochloroform, m.p. 189°-191°.

Workup

  1. customThe solvent was then removed by evaporation in vacuo
  2. washwashed with aqueous sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica eluting with methylene chloride
  6. additioncontaining methanol (0% up to 2%)
  7. customevaporated

Sources & evidence

ORD record
ord-d497b3443726499eb3e9e06a9d99cd9f
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

Loading…