Lawesson's reagent → HCID 90421700, compound

HRID 1752612Notes

Reaction equation

HRID 1752612 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:5]2[C:15](=[O:31])[N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=O)[C:4]2=[CH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=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][O:12][CH2:11][CH2:10]2)=[C:5]2[C:15](=[O:31])[N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=[S:41])[C:4]2=[CH:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 78210284HCID 78210284, compound

Product 1

HCID 90421700HCID 90421700, compoundYield 178.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

5-Methyl-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (0.7 g, 1.67 mmol, see Example 1) was dissolved in toluene (20 ml), stirred and heated to 120° C. and Lawesson's reagent (0.338 g, 0.836 mmol) was added. The reaction was stirred at 120° C. for 16 h. The reaction mixture was cooled to r.t., filtered though a pad of silica gel and concentrated to afford the crude title compound (0.65 g, 77% yield), which was used in the next steps without further purification.

Workup

  1. stirringThe reaction was stirred at 120° C. for 16 h
  2. temperatureThe reaction mixture was cooled to r.t.
  3. filtrationfiltered though a pad of silica gel
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c2f4718225c4ffebf3e880a7020d490
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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