Hydrochloric Acid → HCID 178479406, compound

HRID 2289711Notes

Reaction equation

HRID 2289711 reaction equation
Cl.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][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(C)(C)C>O1CCOCC1>[ClH:34].[Cl:34][C:24]1[C:23]2[C:28](=[CH:29][C:20]([S:17]([N:9]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]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 178451236HCID 178451236, compound

Product 1

HCID 178479406HCID 178479406, compoundYield 114%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of HCl (2 mL, 2 M, 4 mmol) was added to a solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(cyclohexylmethyl)glycine t-butyl ester (53 mg, 0.10 mmol) in dioxane (4.0 mL). The mixture was stirred at 23° C. for 18 h and then heated at 50-60° C. for 16 h. On cooling, a white precipitate crashed out of solution. The solid was collected by filtration, triturated with EtOAc and then dried under vacuum to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(cyclohexylmethyl)glycine hydrochloride (26 mg, 0.057 mmol).

Workup

  1. temperatureheated at 50-60° C. for 16 h
  2. temperatureOn cooling
  3. filtrationThe solid was collected by filtration
  4. customtriturated with EtOAc
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6e7ba4fea6c345bb87b3c510f7a46f56
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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