1,4-Dioxane → Ethyl 1-[(4-iodophenyl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

HRID 2067116Notes

Reaction equation

HRID 2067116 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=O)[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:10]2)=[CH:4][CH:3]=1.O1CCOCC1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[S:40])[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 87949Lawesson's reagentHCID 66744748Ethyl 1-[(4-iodophenyl)methyl]-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

Product 1

HCID 86662101Ethyl 1-[(4-iodophenyl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 1-[(4-iodophenyl)methyl]-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate (800 mg, 1.84 mmol) was suspended in toluene (5 mL) and dioxane (5 mL) and placed into a preheated oil bath to 110° C. Lawesson's Reagent (409 mg, 1.01 mmol, 0.55 equiv) was added portionwise over 45 minutes and after an additional 30 minutes at 110° C., the mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol), providing the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol)

Sources & evidence

ORD record
ord-18dc965e353f4e4f933bd45dda7e6ddf
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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