Ethanol → HCID 22674044, compound

HRID 1005705Notes

Reaction equation

HRID 1005705 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:23]([OH:25])[CH3:24].[H-].[Na+].O>CS(C)=O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([NH:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2]([O:25][CH2:23][CH3:24])=[N:3][CH:4]=[CH:5]3)(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24758Sodium hydrideHCID 22674120HCID 22674120, compound

Product 1

HCID 22674044HCID 22674044, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

In dimethyl sulfoxide (1 ml) was dissolved 57 mg of 1-chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline (Example 61). To the mixture were added ethanol (0.1 ml) and 60% sodium hydride (14 mg), followed by heating under stirring at 80° C. for 9 hours. After standing to cool, water was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. Then, the residue was purified by preparative TLC and solidified from isopropyl ether, to give the title compound (21 mg).

Workup

  1. temperatureby heating
  2. temperatureto cool
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThen, the residue was purified by preparative TLC

Sources & evidence

ORD record
ord-594c00821b184c0fbbbe924a54f231d0
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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