Lawesson's reagent → HCID 86592075, compound

HRID 1797656Notes

Reaction equation

HRID 1797656 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:12](=[O:29])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([C:26]([NH2:28])=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:43])=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]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:12](=[O:29])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([C:26]([NH2:28])=[S:43])=[CH:15][CH:14]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22175271HCID 22175271, compound

Product 1

HCID 86592075HCID 86592075, compoundYield 144.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-4-phenyl-1-oxo-1,2-dihydro-6-isoquinolinecarboxamide (4.05 g, 9 mmol) in toluene (50 ml) was added Lawesson's reagent (2.19 g, 5.4 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)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (3.64 g, 86.9%) 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-14b174ef0c00474484a0aaa6e1c39238
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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