Toluene → HCID 59136020, compound

HRID 1960319Notes

Reaction equation

HRID 1960319 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][C:22]=3[N:28]([CH3:37])[S:29]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)(=[O:31])=[O:30])=O)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:54])=CC=1>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([S:54][C:17]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[CH:23][C:22]=4[N:28]([CH3:37])[S:29]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)(=[O:31])=[O:30])=[N:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 59136004N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

Product 1

HCID 59136020HCID 59136020, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.30 g) in a mixed solvent of toluene (60 ml) and tetrahydrofuran (30 ml) was added Lawesson's reagent (1.94 g), and the mixture was heated under reflux for 3 hr. The reaction solution was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=5:95-40:60), and recrystallized from ethyl acetate-hexane to give the title compound (0.063 g, yield 5%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=5:95-40:60)
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e1327520a69d42a9bc7a5bd65b8e0dc0
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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