Water → HCID 22502833, compound

HRID 1814551Notes

Reaction equation

HRID 1814551 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](=[O:28])(=[O:27])[NH:24][CH2:25][CH3:26])=[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:27])[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](=[O:28])(=[O:27])[NH:24][CH2:25][CH3:26])=[CH:21][CH:22]=3)[N:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 108982-BromoethanolHCID 22502803HCID 22502803, compound

Product 1

HCID 22502833HCID 22502833, compound

Procedure

The resulting 1-(piperazin-1-yl)-3-[4-(N-ethylsulfamoyl)phenyl]isoquinoline (0.49 g) was dissolved in N,N-dimethylformamide (10 ml), followed by the addition of triethylamine (290 ml) and ethylene bromohydrin (185 ml), and the 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 0.20 g of the free compound of the title compound as a colorless powder.

Workup

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

Sources & evidence

ORD record
ord-8f7b74e84b3a45f5a54f814242ac5321
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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