Water → HCID 22503066, compound

HRID 1814554Notes

Reaction equation

HRID 1814554 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:36](Br)[CH2:37][OH:38].[OH2:40].CN(C)[CH:43]=[O:44]>>[C:43]([OH:44])(=[O:24])[C:37]([OH:38])=[O:40].[OH:38][CH2:37][CH2:36][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:17]3[CH:18]=[CH:19][C:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:21][CH:22]=3)[N:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 108982-BromoethanolHCID 22503392HCID 22503392, compound

Product 1

HCID 22503066HCID 22503066, compound

Procedure

The resulting 1-(piperazin-1-yl)-3-[4-(propylsulfonyl)phenyl]isoquinoline (0.61 g) was dissolved in N,N-dimethylformamide (10 ml), followed by the addition of triethylamine (401 μl) and ethylene bromohydrin (255 μl), and the resulting reaction mixture was reacted at 50° C. overnight in nitrogen atmosphere. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water (four times) and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.59 g of the free compound of the title compound as a colorless powder.

Workup

  1. customthe resulting reaction mixture
  2. customwas reacted at 50° C. overnight in nitrogen atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water (four times) and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-07cc261c3415498e8943d929e0ba6f69
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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