Hydrochloric Acid → HCID 178482301, compound

HRID 2289788Notes

Reaction equation

HRID 2289788 reaction equation
C([O:3][C:4](=[O:30])[C:5]1([CH2:29][CH2:28][CH2:27][CH2:26]1)[N:6]([S:8]([C:11]1[CH:20]=[C:19]2[C:14]([C:15]([Cl:25])=[CH:16][N:17]=[C:18]2[NH:21][C:22]([NH2:24])=[NH:23])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7])C.Cl>[OH-].[Na+].CO>[ClH:25].[Cl:25][C:15]1[C:14]2[C:19](=[CH:20][C:11]([S:8]([N:6]([CH3:7])[C:5]3([C:4]([OH:30])=[O:3])[CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:9])=[O:10])=[CH:12][CH:13]=2)[C:18]([NH:21][C:22]([NH2:24])=[NH:23])=[N:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178470337HCID 178470337, compound

Product 1

HCID 178482301HCID 178482301, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(methyl)cycloleucine ethyl ester (80 mg, 0.176 mmol) in NaOH (1 ml, 2N) and MeOH (10 ml) was stirred at 70° C. for 18 h. The cooled mixture was neutralised using HCl (2N), and the MeOH was removed in vacuo. The resulting precipitate was filtered off, washed with water and re-dissolved in concentrated HCl. This solution was evaporated in vacuo, azeotroped with toluene, the residue dissolved in EtOH and filtered. The filtrate was evaporated in vacuo and the resulting solid recrystallised from i-PrOH, to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(methyl)cycloleucine hydrochloride (18 mg, 0.039 mmol) as a yellow solid.

Workup

  1. customthe MeOH was removed in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water
  4. dissolutionre-dissolved in concentrated HCl
  5. customThis solution was evaporated in vacuo
  6. customazeotroped with toluene
  7. dissolutionthe residue dissolved in EtOH
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo
  10. customthe resulting solid recrystallised from i-PrOH

Sources & evidence

ORD record
ord-786e95f3628c49bb9cef1745d1afc8e3
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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