Lawesson's reagent → HCID 90421943, compound

HRID 1752616Notes

Reaction equation

HRID 1752616 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[C:5]2[C:17](=[O:33])[N:18]([CH2:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[C:19](=O)[C:4]2=[CH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[C:5]2[C:17](=[O:33])[N:18]([CH2:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[C:19](=[S:43])[C:4]2=[CH:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86295633HCID 86295633, compound

Product 1

HCID 90421943HCID 90421943, compoundYield 120.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5-methyl-7-(1,1-dioxo-thiomorpholin-4-yl)-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (0.8 g, 1.715 mmol, see Example 3) in toluene (30 ml) was heated to 120° C., Lawesson's reagent (0.347 g, 0.857 mmol) was added and the reaction was stirred at 120° C. for 16 h. The solvent was removed and the resulting mixture was purified on a silica column (DCM/MeOH=50:1) to afford the title compound (0.5 g, 60% yield).

Workup

  1. customThe solvent was removed
  2. customthe resulting mixture was purified on a silica column (DCM/MeOH=50:1)

Sources & evidence

ORD record
ord-52535e54de1b43bcbd114cdf02b549c8
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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