Hydrochloric Acid → HCID 178449964, compound

HRID 2289792Notes

Reaction equation

HRID 2289792 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][CH2:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21]CC)=[O:20])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[C:6]([NH:26][C:27]([NH2:29])=[NH:28])=[N:5][CH:4]=1.CO.Cl>[OH-].[Na+]>[ClH:2].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][CH2:17][C:18]([CH3:25])([CH3:24])[C:19]([OH:21])=[O:20])(=[O:14])=[O:15])=[CH:10][CH:11]=2)[C:6]([NH:26][C:27]([NH2:29])=[NH:28])=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178471503HCID 178471503, compound

Product 1

HCID 178449964HCID 178449964, compoundYield 166.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 3-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}-2,2-dimethylpropanoate hydrochloride (28 mg, 0.06 mmol) in NaOH solution (2N, 0.5 ml), and MeOH (1 ml), was stirred at 75° C. for 24 h. The cooled mixture was acidified to pH 6 using HCl (2N), concentrated in vacuo to remove the MeOH, and the resulting precipitate filtered, washed with water and dried. The solid was suspended in a MeOH/EtOAc solution, ethereal HCl added, and the mixture evaporated in vacuo to afford N-({4-chloro-1-guanidino-7-isoquinolinyl}sulphonyl)-2,2-dimethyl-β-alanine hydrochloride as a white solid (22 mg, 0.05 mmol).

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the MeOH
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water
  5. customdried
  6. additionadded
  7. customthe mixture evaporated in vacuo

Sources & evidence

ORD record
ord-a8d0ed1f329641e19b8e2f0288b22794
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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