Hydrochloric Acid → 7-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride

HRID 269996Notes

Reaction equation

HRID 269996 reaction equation
C(OC(=O)N)(C)(C)C.[NH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]=2[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1)(=[O:15])=[O:14].C(Cl)[Cl:33].Cl>CO>[ClH:33].[NH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]=2[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 866107557-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester

Product 1

HCID 866107577-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester (1.44 g, 3.37 mmol) is dissolved in CH3OH (20 mL) and CH2Cl2 (20 mL) and HCl (37%, 5.0 mL) is added. After the mixture is stirred overnight, the mixture is concentrated and dried under high vacuum to give 1.34 g (100% yield) 7-phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride. Load the product onto ion exchange resin and elute with 1N NH3 in methanol and concentrate to dryness to give the free base.

Workup

  1. concentrationthe mixture is concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-2ad7c83b744e44a1ab02d7b0ba32add4
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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