Lawesson's reagent → HCID 57475961, compound

HRID 1960246Notes

Reaction equation

HRID 1960246 reaction equation
[CH:1]1([CH2:4][N:5]([S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:15]([NH2:17])=O)=[CH:11]3)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCCC1>[CH:1]1([CH2:4][N:5]([S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:15](=[S:35])[NH2:17])=[CH:11]3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57475957HCID 57475957, compound

Product 1

HCID 57475961HCID 57475961, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-[(cyclopropylmethyl)(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (264 mg), Lawesson's reagent (339 mg) and tetrahydrofuran (5 ml) was stirred at 60° C. for 2 hr. The reaction mixture was concentrated lo under reduced pressure, and the residue was subjected to silica gel column chromatography, and eluted with a mixed solvent of ethyl acetate-hexane (1:1) to give the title compound (243 mg, yield 88%) as an amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated lo under reduced pressure
  2. washeluted with a mixed solvent of ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-d66f25cd2d2743f5b578cec81265639b
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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