4-oxothiolane-3-carbonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Keto-4-cyanotetrahydrothiophene (80 g, 0.629 mol) and o-phenylenediamine (68 g, 0.629 mol) were dissolved by heating in 1.5 liters of industrial methylated spirit. To the solution, glacial acetic acid (3 ml) was added, the solution then being heated under reflux with mechanical stirring for 24 hours. The solution was then chilled and filtered to give the title product as a solid, m.p. 163° C. the solution then being heated under reflux The solution was then chilled filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Cyano-3-oxotetrahydrothiophene (1.27 g) was dissolved in acetonitrile (15 ml) with heating and stirring. Hydroxylamine hydrochloride (0.69 g) was added to the refluxing solution and the mixture was refluxed for 11/2hour. After cooling, ether (25 ml) was added and the title compound was filtered off and air-dried. Yield 1.35 g (84%); mp 244°-246°. δ'H nmr (CDCl3 /DMSO-d6) 9.2(br s) 8.55 (d, J=4Hz) 7.85 (d, J=4Hz). with heating the mixture was refluxed for 11/2hour After cooling the title compound was filtered off air-dried

反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-oxotetrahydrothiophene-3-carbonitrile (0.50 g, 3.9 mmol) in anhydrous acetone (7.8 mL) was added potassium carbonate (1.63 g, 11.8 mmol), followed by iodomethane (0.56 g, 3.9 mmol). The resulting mixture was stirred at 35° C. for 1 hour. The mixture was cooled to ambient temperature, filtered, and carefully concentrated in vacuo to afford the title compound. The residue was carried forward without further purification. The mixture was cooled to ambient temperature filtered carefully concentrated in vacuo

反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-oxotetrahydrothiophene-3-carbonitrile (0.50 g, 3.9 mmol) in anhydrous acetone (7.8 mL) was added potassium carbonate (1.63 g, 11.8 mmol), followed by iodomethane (0.56 g, 3.9 mmol). The resulting mixture was stirred at 35° C. for 1 hour. The mixture was cooled to ambient temperature, filtered, and carefully concentrated in vacuo to afford the title compound. The residue was carried forward without further purification. The mixture was cooled to ambient temperature filtered carefully concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Keto-4-cyanotetrahydrothiophene (80 g, 0.629 mol) and o-phenylenediamine (68 g, 0.629 mol) were dissolved by heating in 1.5 liters of industrial methylated spirit. To the solution, glacial acetic acid (3 ml) was added, the solution then being heated under reflux with mechanical stirring for 24 hours. The solution was then chilled and filtered to give the title product as a solid, m.p. 163° C. the solution then being heated under reflux The solution was then chilled filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Cyano-3-oxotetrahydrothiophene (1.27 g) was dissolved in acetonitrile (15 ml) with heating and stirring. Hydroxylamine hydrochloride (0.69 g) was added to the refluxing solution and the mixture was refluxed for 11/2hour. After cooling, ether (25 ml) was added and the title compound was filtered off and air-dried. Yield 1.35 g (84%); mp 244°-246°. δ'H nmr (CDCl3 /DMSO-d6) 9.2(br s) 8.55 (d, J=4Hz) 7.85 (d, J=4Hz). with heating the mixture was refluxed for 11/2hour After cooling the title compound was filtered off air-dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Keto-4-cyanotetrahydrothiophene (80 g, 0.629 mol) and o-phenylenediamine (68 g, 0.629 mol) were dissolved by heating in 1.5 liters of industrial methylated spirit. To the solution, glacial acetic acid (3 ml) was added, the solution then being heated under reflux with mechanical stirring for 24 hours. The solution was then chilled and filtered to give the title product as a solid, m.p. 163° C. the solution then being heated under reflux The solution was then chilled filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Keto-4-cyanotetrahydrothiophene (80 g, 0.629 mol) and o-phenylenediamine (68 g, 0.629 mol) were dissolved by heating in 1.5 litres of industrial methylated spirit. To the solution, glacial acetic acid (3 ml) was added, the solution then being heated under reflux with mechanical stirring for 24 hours. The solution was then chilled and filtered to give the title product as a solid, m.p. 163° C. the solution then being heated under reflux The solution was then chilled filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Cyano-3-tetrahydrothiophenone (5.0 g) was dissolved in N,N-dimethylformamide (30 ml), then, sodium hydride (oil, about 60%, 950 mg) was added under ice cooling, and stirred at the same temperature for 30 minutes. Then, to the mixture was added a solution of methyl 2-(4-bromomethylphenyl)propionate (10.1 g) in N,N-dimethylformamide (10.0 ml) under ice cooling, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (5.5 g, 46%). the reaction mixture was stirred overnight at room temperature The reaction mixture was quenched with water extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

反応条件: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-oxotetrahydrothiophene-3-carbonitrile (77.6 mg, 0.61 mmol) and 4-(6-phenylpyridin-3-yl)-1H-pyrazol-5-amine (144 mg, 0.61 mmol) in toluene (10 mL) was heated at 115° C. overnight. Concentration and purification with prep-LC provided 3-(6-phenylpyridin-3-yl)-5,7-dihydropyrazolo[1,5-a]thieno[3,4-d]pyrimidin-8-amine: LCMS tR=1.48 Min (5 min run, UV254mn), Mass calculated for, M+345.1, observed LC/MS m/z 346.1 (M+H). Concentration and purification

反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-oxotetrahydrothiophene-3-carbonitrile (0.50 g, 3.9 mmol) in anhydrous acetone (7.8 mL) was added potassium carbonate (1.63 g, 11.8 mmol), followed by iodomethane (0.56 g, 3.9 mmol). The resulting mixture was stirred at 35° C. for 1 hour. The mixture was cooled to ambient temperature, filtered, and carefully concentrated in vacuo to afford the title compound. The residue was carried forward without further purification. The mixture was cooled to ambient temperature filtered carefully concentrated in vacuo