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

HRID 654191Notes

Reaction equation

HRID 654191 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 foam, 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-4e4d0bc15cbd42d896e13a6e17c8b912
Source dataset
uspto-grants-1992_07
Patent number
US05130334

Reaction notes

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