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

HRID 14632Notes

Reaction equation

HRID 14632 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:29])[NH:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:11][N:10]=1)(C)(C)C.Cl>CCOC(C)=O>[CH3:28][O:27][CH2:26][CH2:25][NH:24][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:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68613214[6,8-Dimethoxy-4-(2-methoxy-ethylcarbamoyl)-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 468468291-Aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid (2-methoxy-ethyl)-amideYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As described in example 1, 92 mg of [6,8-dimethoxy-4-(2-methoxy-ethylcarbamoyl)-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester was treated with HCl in EtOAc to give 22 mg (32%) of 1-aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid (2-methoxy-ethyl)-amide. H1-NMR (Free base) (CDCl3): δ, 8.47 (s, 1H), 7.33 (s, 1H), 6.63 (s, 1H), 6.57 (s, 1H), 4.45 (s, 2H), 3.97 (s, 3H), 3.93 (s, 3H), 3.73 (q, J=4.8 Hz, 2H), 3.63 (d, J=5.1 Hz, 2H), 3.61 (s, 3H), 3.40 (s, 3H); MS: APCI (M+H) calc'd for C16H21N3O4+H 320.4; found 320.2.

Sources & evidence

ORD record
ord-dab59047831443278f2c5c38f30ec238
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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