Hydrochloric Acid → 1-Aminomethyl-6,7-dimethoxy-isoquinoline-4-carboxylic acid benzyl-methyl-amide hydrochloride

HRID 14660

Reaction equation

HRID 14660 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])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([C:23](=[O:33])[N:24]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:25])=[CH:11][N:10]=1)(C)(C)C.[ClH:35]>CCOC(C)=O>[ClH:35].[CH2:26]([N:24]([CH3:25])[C:23]([C:12]1[C:13]2[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[C:9]([CH2:8][NH2:7])=[N:10][CH:11]=1)=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68613162[4-(Benzyl-methyl-carbamoyl)-6,7-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 468471661-Aminomethyl-6,7-dimethoxy-isoquinoline-4-carboxylic acid benzyl-methyl-amide hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As described in example 1, a solution of [4-(benzyl-methyl-carbamoyl)-6,7-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester (82 mg) was treated with HCl in EtOAc to give 56 mg (79%) of 1-aminomethyl-6,7-dimethoxy-isoquinoline-4-carboxylic acid benzyl-methyl-amide hydrochloride: 1H NMR (DMSO-d6) δ 2.68 (s, 2H), 3.67 (s, 2H), 3.91 (s, 1H), 3.97 (s, 3H), 4.33 (br s, 1H), 4.67-4.72 (m, 3H), 6.80 (s, 1H), 7.04-7.51 (m, 6H), 8.36 (d, 1H, J=4.26 Hz), 8.56-8.63 (m, 3H); MS: APCI (M+H) calc'd for C21H23N3O3 366.2; found 366.1.

Sources & evidence

ORD record
ord-0461c1eb7f0f43598cc77b94c823513c
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Linked notes

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