2-Methoxyethylamine → {6,7-Dimethoxy-4-[(2-methoxy-ethylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester

HRID 14678

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24][C:25](O)=[O:26])=[CH:12][N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][O:29][CH2:30][CH2:31][NH2:32]>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24][C:25](=[O:26])[NH:32][CH2:31][CH2:30][O:29][CH3:28])=[CH:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 68613423[1-(Tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid

Product 1

HCID 68613520{6,7-Dimethoxy-4-[(2-methoxy-ethylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester

Procedure

As described in Example 1, 60 mg of [1-(tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid was coupled with 2-methoxy-ethylamine to give 40 mg of {6,7-dimethoxy-4-[(2-methoxy-ethylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester. H1-NMR (CDCl3): δ, d 8.21 (s, 1H), 7.40 (s, 1H), 7.25 (s, 1H), 6.17 (br s, 1H), 5.74 (br s, 1H), 4.89 (d, J=4.7 Hz, 2H), 4.03 (s, 6H), 3.89 (s, 2H), 3.36 (m, 4H), 3.17 (s, 3H), 1.51 (s, 9H); MS: APCI (M+H) calc'd for C22H31N3O6+H 434.5; found 434.0.

Sources & evidence

ORD record: ord-6be31d93dbf84cfc814253225ac21518
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732446B1

Linked notes

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