Lawesson's reagent → HCID 86592074, compound

HRID 1797646Notes

Reaction equation

HRID 1797646 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:12](=[O:28])[C:13]2[C:18]([C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][C:16]([C:25]([NH2:27])=O)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[N:11]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:12](=[O:28])[C:13]2[C:18]([C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][C:16]([C:25]([NH2:27])=[S:42])=[CH:15][CH:14]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22175840HCID 22175840, compound

Product 1

HCID 86592074HCID 86592074, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-[[(tert-butoxycarbonyl)amino]methyl]-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinecarboxamide (0.44 g, 1 mmol) in toluene (20 ml) was added Lawesson's reagent (0.24 g, 0.6 mmol), and the mixture was refluxed under heating for 1 h. The reaction mixture was purified by silica gel column chromatography to give tert-butyl[6-(aminothiocarbonyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.18 g, 39.1%) as crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 h
  3. customThe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb0a6334848b48319771981fa7b2450f
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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