Water → HCID 22502833, compound

HRID 1006993Notes

Reaction equation

HRID 1006993 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-c4fef9c46b434a37a06d1d2185c44452
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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