Hydrochloric Acid → HCID 178480492, compound

HRID 2289784Notes

Reaction equation

HRID 2289784 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]3([C:23]([O:25]C)=[O:24])[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([NH:27][C:28]([NH2:30])=[NH:29])=[N:4][CH:3]=1.[OH-].[Na+].Cl>CO>[ClH:1].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]3([C:23]([OH:25])=[O:24])[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([NH:27][C:28]([NH2:30])=[NH:29])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178499192HCID 178499192, compound

Product 1

HCID 178480492HCID 178480492, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[({4-chloro-1-guanidino-7-isoquinolinyl}sulphonyl)amino]-1-methyl-4-piperidinecarboxylate (100 mg, 0.22 mmol) in aqueous NaOH (2 ml, 2M, 4 mmol) and MeOH (5 ml) was stirred at 60° C. for 42 h. The cooled solution was neutralised using 2M HCl, and the mixture concentrated in vacuo, until precipitation occurred. The solid was filtered, dried and dissolved in concentrated HCl, and the solution evaporated in vacuo. The resulting solid was triturated with Et2O, then i-PrOH, and dried under vacuum, to give 4-[({4-chloro-1-guanidino-7-isoquinolinyl}sulphonyl)amino]-1-methyl-4-piperidinecarboxylic acid hydrochloride (18 mg, 0.035 mmol).

Workup

  1. concentrationthe mixture concentrated in vacuo, until precipitation
  2. filtrationThe solid was filtered
  3. customdried
  4. dissolutiondissolved in concentrated HCl
  5. customthe solution evaporated in vacuo
  6. customThe resulting solid was triturated with Et2O
  7. dry with materiali-PrOH, and dried under vacuum

Sources & evidence

ORD record
ord-9fe4640ba2e04ba58f4beefa3207b4b9
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

Loading…