Hydrochloric Acid → N-[(5-isoquinolyl)sulfonyl]-1,3-cyclohexanediamine

HRID 10597Notes

Reaction equation

HRID 10597 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][S:16]([C:19]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:20]=2[CH:21]=[CH:22][N:23]=[CH:24]3)(=[O:18])=[O:17])[CH2:10]1)=O)(C)(C)C.Cl>CO>[CH:24]1[C:25]2[C:20](=[C:19]([S:16]([NH:15][CH:11]3[CH2:12][CH2:13][CH2:14][CH:9]([NH2:8])[CH2:10]3)(=[O:17])=[O:18])[CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21979834N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-cyclohexanediamine

Product 1

HCID 21979764N-[(5-isoquinolyl)sulfonyl]-1,3-cyclohexanediamineYield 108.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 54 (6 g) obtained above was added to a 10% hydrogen chloride solution in methanol (50 ml) and stirred under reflux by heating for 1.5 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in a mixed solvent of dichloromethane and ethanol, added with saturated aqueous potassium carbonate and vigorously shaken. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the title compound (4.9 g).

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 1.5 hours
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in a mixed solvent of dichloromethane and ethanol
  5. additionadded with saturated aqueous potassium carbonate
  6. stirringvigorously shaken
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3eab5bbdfa2e416eae1d6d8b01877451
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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