Lawesson's reagent → HCID 86662105, compound

HRID 2067124Notes

Reaction equation

HRID 2067124 reaction equation
O=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[CH:23][CH:22]=[N:21]3)=[CH:16][CH:15]=2)[C:4]2[CH:25]=[CH:26][S:27][C:3]1=2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>O1CCOCC1.C1(C)C=CC=CC=1>[S:37]=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[CH:23][CH:22]=[N:21]3)=[CH:16][CH:15]=2)[C:4]2[CH:25]=[CH:26][S:27][C:3]1=2

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 66745354HCID 66745354, compound

Product 1

HCID 86662105HCID 86662105, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 4-oxo-1-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-1,4-dihydrothieno[3,2-c]pyridazine-3-carboxylate (37 mg, 0.097 mmol) suspended in dioxane (5 mL) and toluene (5 mL), placed into an oil bath preheated at 110° C. and treated with Lawesson's Reagent (39 mg, 0.097 mmol, 1 equiv) portionwise over 10 minutes. The mixture was heated for an additional 30 minutes, cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 25:75; hexanes:ethyl acetate), providing the titled compound as a brown oil.

Workup

  1. custompreheated at 110° C.
  2. temperatureThe mixture was heated for an additional 30 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel gradient chromatography (100:0 to 25:75; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-fa94cd4662274547b0d2f23df4a0cbb3
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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