Hydrochloric Acid → 1-Chloro-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride

HRID 2219203Notes

Reaction equation

HRID 2219203 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[C:16]2[CH:17]=[CH:18][N:19]=[C:20]([Cl:25])[C:21]=2[CH:22]=[CH:23][CH:24]=1)(=[O:14])=[O:13])(C)(C)C>C(Cl)Cl>[ClH:25].[NH2:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[C:16]2[CH:17]=[CH:18][N:19]=[C:20]([Cl:25])[C:21]=2[CH:22]=[CH:23][CH:24]=1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21979959[2-(1-Chloro-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 866109261-Chloro-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochlorideYield 198.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A small stream of hydrogen chloride is bubbled through a stirred solution of [2-(1-chloro-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (6.74 g, 17.5 mmol) in anhydrous CH2Cl2 (100 mL) at 0° C. under nitrogen for 10 minutes. The resultant white suspension is allowed to stir at ambient temperature for 1 hour. After filtration and vacuum drying at 50° C., 5.61 g (17.4 mmol, 100% yield) of the title compound is obtained as a white powder. ESIMS: m/z 286 [(M+H)+, 35Cl], 288 [(M+H)+, 37Cl]. Analysis for C11H13Cl2N3O2S.0.3H2O: calcd: C, 40.33; H, 4.18; N, 12.83; found: C, 40.34; H, 3.80; N, 12.43.

Workup

  1. filtrationAfter filtration and vacuum
  2. customdrying at 50° C.

Sources & evidence

ORD record
ord-821d0073987c4501888f48f71c30ac6b
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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