Ethanol → HCID 22674044, compound

HRID 1173147Notes

Reaction equation

HRID 1173147 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

1-Chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline (Synthetic Example 61b, 57 mg) was dissolved in dimethyl sulfoxide (1 ml). Ethanol (0.1 ml) and 60% sodium hydride (14 mg) were added thereto, followed by heating under stirring at 80° C. for 9 hours. After cooling as it was, water was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by preparative TLC and solidified using isopropyl ether, to give the title compound (21 mg).

Workup

  1. temperatureby heating
  2. temperatureAfter cooling as it
  3. extractionby extracting with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent
  7. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-aede77dcac2a4f2d829b57791e8552c1
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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