Hydrochloric Acid → 1-Aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid 4-methoxy-benzylamide hydrochloride

HRID 14634Notes

Reaction equation

HRID 14634 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:34])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:11][N:10]=1)(C)(C)C.[ClH:36]>CCOC(C)=O>[ClH:36].[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][NH:24][C:23]([C:12]2[C:13]3[C:18](=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)[C:9]([CH2:8][NH2:7])=[N:10][CH:11]=2)=[O:34])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68614475[6,8-Dimethoxy-4-(4-methoxy-benzylcarbamoyl)-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 686134331-Aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid 4-methoxy-benzylamide hydrochlorideYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As described in example 1, 46 mg of [6,8-dimethoxy-4-(4-methoxy-benzylcarbamoyl)-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester was treated with HCl in EtOAc to give 20 mg (54%) of 1-aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid 4-methoxy-benzylamide hydrochloride. H1-NMR (DMSO): δ 9.26 (br s, 3H), 8.41 (s, 1H), 8.38 (br s, 1H), 7.31 (d, J=8.2 Hz, 2H), 7.09 (s, 1H), 6.90 (d, J=8.2 Hz, 2H), 6.81 (s, 1H), 4.67 (d, J=5.1 Hz, 2H), 4.44 (d, J=5.5 Hz, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 3.71 (s, 3H); MS: APCI (M+H) calc'd for C21H23N3O4+H 382.4; found 382.2.

Sources & evidence

ORD record
ord-ac29ce012c0c424aaab5aca11cddc64d
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

Loading…