Sodium Iodide → HCID 15157853, compound

HRID 1614580Notes

Reaction equation

HRID 1614580 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([OH:18])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.[I-].[Na+].C(N(CC)CC)C.[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH2:37][CH2:38]Br)=[O:36])=[CH:31][CH:30]=1>CN(C)C=O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH2:37][CH2:38][N:2]([CH2:3][CH:4]([OH:18])[CH2:5][O:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]3)[CH3:1])=[O:36])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 10106057HCID 10106057, compoundHCID 20095465HCID 20095465, compound

Product 1

HCID 15157853HCID 15157853, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension (50 ml) of 6-(3-methylamino-2-hydroxypropoxy)carbostyril (3.0 g), sodium iodide (11.8 g), triethylamine (2.2 ml) and 2-(4-fluorophenylsulfinyl)ethyl bromide (3.9 g) in dimethylformamide is heated with stirring at 80°-90° C. for 5 hours. After concentration under reduced pressure, the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol:ammonium hydroxide=200:10:1-150:10:1) and recrystallized from dichloromethane-diethylether to give 6-[3-{N-[2-(4-fluorophenylsulfinyl)ethyl]-N-methylamino)-2-hydroxypropoxy]carbostyril (0.7 g), as white powder, m.p. 126°-129° C.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol:ammonium hydroxide=200:10:1-150:10:1)
  3. customrecrystallized from dichloromethane-diethylether

Sources & evidence

ORD record
ord-35b5b7a411424ecea4743501e5ba4032
Source dataset
uspto-grants-1993_03
Patent number
US05198448

Reaction notes

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