Hydrochloric Acid → HCID 178512673, compound

HRID 2289761Notes

Reaction equation

HRID 2289761 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([C:23]([O:25]CC)=[O:24])[CH2:19][CH2:18]3)(=[O:15])=[O:14])=[CH:10][CH:11]=2)[C:6]([NH:28][C:29]([NH2:31])=[NH:30])=[N:5][CH:4]=1>O1CCOCC1>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]3)(=[O:14])=[O:15])=[CH:10][CH:11]=2)[C:6]([NH:28][C:29]([NH2:31])=[NH:30])=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178472460HCID 178472460, compound

Product 1

HCID 178512673HCID 178512673, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl (5 mL, 2 M, 10 mmol) was added to a solution of ethyl trans-4-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate (55 mg, 0.121 mmol) in dioxane (5.0 mL) and the mixture was heated at reflux for 2 h. The solvents were evaporated in vacuo and the residue was purified by column chromatography upon MCI gel (CHP 20P) using water-MeOH (100:0 to 20:80) as eluant to give trans-4-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}-cyclohexanecarboxylic acid. This material was dissolved in dilute HCl (20 mL, 0.1 M), the solvents were evaporated in vacuo, and the residue triturated with Et2O to give trans-4-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylic acid hydrochloride (35 mg, 0.067 mmol) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe solvents were evaporated in vacuo
  4. customthe residue was purified by column chromatography upon MCI gel (CHP 20P)

Sources & evidence

ORD record
ord-6d0199dc29ef4be2b71d8ab38fe68f45
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

Loading…