Diethyl Ether → (4-Amino-6,7-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

HRID 14665Notes

Reaction equation

HRID 14665 reaction equation
C(OC(=O)[NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N:13][CH:12]=1)C1C=CC=CC=1.C1COCC1.CCOCC>CCO.[Pd]>[C:30]([O:29][C:27](=[O:28])[NH:26][CH2:25][C:14]1[C:15]2[C:20](=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[C:11]([NH2:10])=[CH:12][N:13]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 59341103[1-(tert-Butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-carbamic acid benzyl ester

Product 1

HCID 59341104(4-Amino-6,7-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [1-(tert-Butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-carbamic acid benzyl ester, in 45 mL of EtOH and 20 mL THF was hydrogenated at 1 atm (balloon) over 60 mg of 10% Pd—C for 3 h. The catalyst was removed by filtration through a plug of celite and the filtrate was concentrated to give a white film. Trituration with ether gave 534 mg (89%) of the 4-aminoisoquinoline as a white granular solid. H1-NMR (CDCl3): δ 7.84 (s, 1H), 7.36 (s, 1H), 7.02 (s, 1H), 6.00 (s, 1H), 4.78 (d, J=5.1 Hz, 1H), 4.03 (s, 3H), 4.01 (s, 3H), (s, 1H), 3.89 (s, 2H), 1.48 (s, 9H). MS: APCI (M+H) calc' d for C18H24N2O4+H 334.4; found 334.0.

Workup

  1. customThe catalyst was removed by filtration through a plug of celite
  2. concentrationthe filtrate was concentrated
  3. customto give a white film

Sources & evidence

ORD record
ord-6fd92c6761c94d75acfc12d1a3a2e85f
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

Loading…