Lawesson's reagent → HCID 86635813, compound

HRID 240532Notes

Reaction equation

HRID 240532 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[C:14]([N:18]3[CH2:22][C@@H:21]4[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C@@H:20]4[CH2:19]3)[CH:15]=[N:16][CH:17]=2)=O)[CH:5]=[C:6]([F:8])[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[C:14]([N:18]3[CH2:22][C@@H:21]4[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C@@H:20]4[CH2:19]3)[CH:15]=[N:16][CH:17]=2)=[S:42])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67266158HCID 67266158, compound

Product 1

HCID 86635813HCID 86635813, compoundYield 191.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

The product from Example 42A (60 mg, 0.14 mmol) and Lawesson's reagent (27 mg, 0.068 mmol) were combined with toluene (3 mL) and stirred at 110° C. for 18 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and purified by silica gel flash chromatography (EtOAc, Rf=0.35) to provide the title compound (60 mg, 97%). MS (APCI) m/z 387 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. custompurified by silica gel flash chromatography (EtOAc, Rf=0.35)

Sources & evidence

ORD record
ord-afdadc64b68445299a9a4bd0be27e0bf
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Reaction notes

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