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

HRID 14674

Reaktionsgleichung

Reaktionsgleichung von HRID 14674
[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][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1.C(P(=O)(OCC)OCC)#N>>[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:35][CH2:34][C:33]2[CH:36]=[CH:37][C:30]([O:29][CH3:28])=[CH:31][CH:32]=2)=[CH:12][N:11]=1)([CH3:2])([CH3:4])[CH3:3]

Komponenten

4

Edukt 3

HCID 754524-MethoxybenzylamineHCID 76257Diethyl cyanophosphonateHCID 68613423[1-(Tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid

Produkt 1

HCID 59341099{6,7-Dimethoxy-4-[(4-methoxy-benzylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl esterAusbeute 80,7 %

Versuchsvorschrift

[1-(tert-Butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid (70 mg, 0.19 mmol) was treated with 4-methoxybenzylamine (31 mg, 0.22 mmol), diethyl cyanophosphonate (36 mg, 0.22 mmol), and TEA (38 mg, 0.37 mmol) according to the procedure described in example 1E to give {6,7-dimethoxy-4-[(4-methoxy-benzylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester (74 mg, 80.7%). H1-NMR (CDCl3): 8.19 (s, 1H), 7.37 (s, 1H), 7.18 (s, 1H), 6.97 (d, 2H, J=8.8 Hz), 6.73 (d, 2H, J=8.5 Hz), 6.14 (m, 1H), 5.62 (m, 1H), 4.87 (d, 2H, J=4.3 Hz), 4.26 (d, 2H, J=6.0 Hz), 4.03 (s, 2H), 3.94, 3.91, and 3.75 (s, 3H each), 1.50 (s, 9H); MS: APCI (M+H) calc'd for C27H33N3O6+H 496.6; found 496.0.

Quellen und Nachweise

ORD-Eintrag
ord-567fb7c4f76949ebbf825a1a68c5c828
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732446B1

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