Lawesson's reagent → HCID 59331536, compound

HRID 1881817Notes

Reaction equation

HRID 1881817 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23]([NH2:25])=O)=[C:20]([CH3:26])[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCCC1>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23](=[S:36])[NH2:25])=[C:20]([CH3:26])[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59331295HCID 59331295, compound

Product 1

HCID 59331536HCID 59331536, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution (10 mL) of 5-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-3-methyl-1H-pyrrole-2-carboxamide (135 mg) in tetrahydrofuran was added Lawesson's reagent (156 mg), and the mixture was stirred for 3 hr at 55° C. After cooling to room temperature, the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography, and the title compound (120 mg, yield 86%) was m obtained as yellow amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 391 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-bdf1b89976134fa386db6d55f709dd4c
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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