Water → HCID 22674145, compound

HRID 1005703Notes

Reaction equation

HRID 1005703 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.CO.[CH3:25][NH:26][CH3:27].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]([N:26]([CH3:27])[CH3:25])=[N:3][CH:4]=[CH:5]3)(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22497844Dimethylamine methanolHCID 22674120HCID 22674120, compound

Product 1

HCID 22674145HCID 22674145, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

In dimethyl sulfoxide (1 ml) was dissolved 60 mg of 1-chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline (Example 61). To the mixture was added 50% dimethylamine methanol solution (0.04 ml), followed by heating under stirring at 80° C. for 10 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. The residue was purified by preparative TLC and solidified from isopropyl ether, to give the title compound (17 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. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-6084891e54224e5ea7f2efaa7b293832
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

Loading…