Hydrochloric Acid → 1-Aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid benzyl-(2-dimethylamino-ethyl)-amide

HRID 14645Notes

Reaction equation

HRID 14645 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[CH:16][C:17]=2[O:19][CH3:20])[C:12]([C:23](=[O:37])[N:24]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[CH:11][N:10]=1)(C)(C)C.Cl>CCOC(C)=O>[CH2:30]([N:24]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:23]([C:12]1[C:13]2[C:18](=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=2)[C:9]([CH2:8][NH2:7])=[N:10][CH:11]=1)=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68613386{4-[Benzyl-(2-dimethylamino-ethyl)-carbamoyl]-6,8-dimethoxy-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 468469411-Aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid benzyl-(2-dimethylamino-ethyl)-amideYield 100.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As described in example 1, 91 mg of {4-[benzyl-(2-dimethylamino-ethyl)-carbamoyl]-6,8-dimethoxy-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester was treated with HCl in EtOAc to give 74 mg (>100%) of 1-aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid benzyl-(2-dimethylamino-ethyl)-amide MS: APCI (M+H) calc'd for C24H30N4O3+H 423.5; found 423.2.

Sources & evidence

ORD record
ord-1bf089bb81f44c9b9073166a534fb480
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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