Lawesson's reagent → HCID 11385549, compound

HRID 1831737Notes

Reaction equation

HRID 1831737 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:22]3[CH2:31][CH2:30][CH2:29][CH:23]3[C:24](=O)[NH:25][C:26]=2[CH:27]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>COCCOC>[C:1]([O:5][C:6]([N:8]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:22]3[CH2:31][CH2:30][CH2:29][CH:23]3[C:24](=[S:41])[NH:25][C:26]=2[CH:27]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 15429328HCID 15429328, compound

Product 1

HCID 11385549HCID 11385549, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 75 mg (0.17 mmol) of 7-(N-tert-butoxycarbonyl-3-chlorobenzyl-amino)methyl-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 5 ml of 1,2-dimethoxyethane is mixed with 138 mg (0.34 mmol) of Lawesson's reagent. After 1.5 hours at room temperature, the batch is refluxed for 0.75 hour and then concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 65 mg of product.

Workup

  1. temperaturethe batch is refluxed for 0.75 hour
  2. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-b35670aaee5745b8bc67232dbeb6fca0
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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