Hydrochloric Acid → HCID 178478801, compound

HRID 2289724Notes

Reaction equation

HRID 2289724 reaction equation
[ClH:1].C([O:6][C:7](=[O:35])[CH2:8][N:9]([S:17]([C:20]1[CH:29]=[C:28]2[C:23]([C:24]([Cl:34])=[CH:25][N:26]=[C:27]2[NH:30][C:31]([NH2:33])=[NH:32])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)(C)(C)C>O1CCOCC1>[ClH:34].[ClH:1].[Cl:34][C:24]1[C:23]2[C:28](=[CH:29][C:20]([S:17]([N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:8][C:7]([OH:35])=[O:6])(=[O:18])=[O:19])=[CH:21][CH:22]=2)[C:27]([NH:30][C:31]([NH2:33])=[NH:32])=[N:26][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451241HCID 178451241, compound

Product 1

HCID 178478801HCID 178478801, compoundYield 145.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of HCl (3 mL, 2 M, 6 mmol) was added to a solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(2-pyridylmethyl)glycine t-butyl ester (115 mg, 0.23 mmol) in dioxane (5.0 mL) and the mixture was heated at 60° C. for 18 h. The solvents were evaporated in vacuo and the residue triturated with hot EtOAc to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(2-pyridylmethyl)glycine dihydrochloride (95 mg, 0.167 mmol) as an off-white solid.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue triturated with hot EtOAc

Sources & evidence

ORD record
ord-382b6f01720349fc8d8ae041b4cdab73
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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