tert-Butyl [3-(7-amino-4,4-dimethyl-8-nitro-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamate → tert-Butyl [3-(7,8-diamino-4,4-dimethyl-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamate

HRID 2253303Notes

Reaction equation

HRID 2253303 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]2[C:5]([C:6]([CH3:41])([CH3:40])[C:7](=[O:39])[N:8]([CH2:16][CH2:17][CH2:18][N:19]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=3)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]2=[O:15])=[CH:4][CH:3]=1>CCO.C1COCC1.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6]([CH3:41])([CH3:40])[C:7](=[O:39])[N:8]([CH2:16][CH2:17][CH2:18][N:19]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=3)[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:9]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 59645476tert-Butyl [3-(7-amino-4,4-dimethyl-8-nitro-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamate

Product 1

HCID 59645485tert-Butyl [3-(7,8-diamino-4,4-dimethyl-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamateYield 83.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl [3-(7-amino-4,4-dimethyl-8-nitro-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamate (3.60 g, 6.31 mmol) and 20% Pd(OH)2/C (0.72 g) in EtOH (100 mL) and THF (10 mL) was stirred under H2 (balloon) for 16 h. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1 to 1:2) to give the title compound (2.85 g, 83% yield).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1 to 1:2)

Sources & evidence

ORD record
ord-a6b35a25b8ad4f7e839f3b39e282e9ff
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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