Hydrochloric Acid → HCID 178479403, compound

HRID 2289754Notes

Reaction equation

HRID 2289754 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([NH:17][C:18]3([C:24]([O:26]C)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:11][CH:12]=2)[C:7]([NH:28][C:29]([NH2:31])=[NH:30])=[N:6][CH:5]=1.Cl>CO>[ClH:3].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([NH:17][C:18]3([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)(=[O:15])=[O:16])=[CH:11][CH:12]=2)[C:7]([NH:28][C:29]([NH2:31])=[NH:30])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178499191HCID 178499191, compound

Product 1

HCID 178479403HCID 178479403, compoundYield 155.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of NaOH (1 mL, 2 M, 2 mmol) was added to a solution of methyl 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate (12 mg, 0.027 mmol) in MeOH (4 mL) and the mixture was heated at 50-60° C. for 4 d. The cooled mixture was neutrilised with dilute HCl (1 mL, 2 M) to give a precipitate. The solid was collected by filtration, with copious water washing, and then triturated with EtOAc. The solid was dissolved in conc. HCl, the solvents were evaporated in vacuo azeptroping with PhMe, and then dried under high vacuum to give 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylic acid hydrochloride (11 mg, 0.021 mmol).

Workup

  1. customto give a precipitate
  2. filtrationThe solid was collected by filtration, with copious water washing
  3. customtriturated with EtOAc
  4. dissolutionThe solid was dissolved in conc. HCl
  5. customthe solvents were evaporated in vacuo
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-61956c032f5445dba3071fa3ff1cc576
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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