氨基硫脲单盐酸盐

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2-ethoxy-4-p-methoxybenzylthio-1-pyrroline (900 mg) and thiosemicarbazide hydrochloride (433 mg) in ethanol (30 ml) was refluxed under heating for 1.5 hours. The reaction solution was evaporated to dryness under reduced pressure, then the residue was distributed between ethyl acetate and 5% aqueous solution of sodium hydroxide and the organic phase was dried over Na2SO4 before the solvent was distilled off under reduced pressure. The resultant residue was passed through a column packed with 25 g of silica gel and eluted with ethyl acetate and thus 230 mg of the objective compound was obtained as colorless foam. under heating for 1.5 hours The reaction solution was evaporated to dryness under reduced pressure the organic phase was dried over Na2SO4 before the solvent was distilled off under reduced pressure eluted with ethyl acetate

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2-ethoxy-4-p-methoxybenzylthio-1-pyrroline (900 mg) and thiosemicarbazide hydrochloride (433 mg) in ethanol (30 ml) was refluxed under heating for 1.5 hours. The reaction solution was evaporated to dryness under reduced pressure, then the residue was distributed between ethyl acetate and 5% aqueous solution of sodium hydroxide and the organic phase was dried over Na2SO4 before the solvent was distilled off under reduced pressure. The resultant residue was passed through a column packed with 25 g of silica gel and eluted with ethyl acetate and thus 230 mg of the objective compound was obtained as colorless foam. under heating for 1.5 hours The reaction solution was evaporated to dryness under reduced pressure the organic phase was dried over Na2SO4 before the solvent was distilled off under reduced pressure eluted with ethyl acetate

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-(tert-Butoxycarbonylamino)acetophenone (3.00 g) was dissolved in methanol (21.0 mL). To the solution was added an aqueous solution (water: 9.0 mL) of thiosemicarbazide hydrochloride (3.11 g, 24.4 mmol) at room temperature. After the mixture was stirred at the same temperature for 30 minutes, water (12.0 mL) was added, and the mixture was stirred at room temperature for 20 minutes and then at 0° C. for 1 hour. The deposited solid was collected by filtration and washed with cooled 50% aqueous methanol (20 mL). The resulting solid was dried at 40° C. under reduced pressure to give seed crystals of 2-(tert-butoxycarbonylamino)acetophenone thiosemicarbazone (3.56 g, yield: 95.1%) as a white solid. the mixture was stirred at room temperature for 20 minutes at 0° C. for 1 hour The deposited solid was collected by filtration washed with cooled 50% aqueous methanol (20 mL) The resulting solid was dried at 40° C. under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared from hydrazine carbothioamide hydrochloride and 1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-ethanone in analogy to the synthesis of example 1 in 60% yield as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 10.53 (s, 1H), 8.88 (dd, 1H), 8.53 (s, 1H), 8.47 (d, 1H), 8.34 (m, 2H), 8.10 (d, 1H), 7.99 (d, 1H), 7.85 (s, 1H), 7.79 (d, 1H), 7.50 (q, 1H), 4.59 (s, 2H), 2.34 (s, 3H). LCMS (method A): [MH]+=394, tR=4.91 min.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared from hydrazine carbothioamide hydrochloride and 1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-ethanone in analogy to the synthesis of example 1 in 60% yield as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 10.53 (s, 1H), 8.88 (dd, 1H), 8.53 (s, 1H), 8.47 (d, 1H), 8.34 (m, 2H), 8.10 (d, 1H), 7.99 (d, 1H), 7.85 (s, 1H), 7.79 (d, 1H), 7.50 (q, 1H), 4.59 (s, 2H), 2.34 (s, 3H). LCMS (method A): [MH]+=394, tR=4.91 min.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thiosemicarbazide hydrochloride (8.30 g, 65.1 mmol) was dissolved in a mixed solvent of methanol (50 mL) and distilled water (50 mL). To the solution was added ethyl benzoylacetate (17.0 mL, 98.2 mmol) and concentrated hydrochloric acid (1.00 mL, 12.0 mmol), and the mixture was stirred at room temperature for 11 hours. The deposited solid was collected by filtration, washed (methanol) and then dried to give 3 phenyl-3-thiosemicarbazonopropionic acid ethyl ester (thiosemicarbazone) (11.1 g, 64%). distilled water (50 mL) The deposited solid was collected by filtration washed (methanol) dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thiosemicarbazide hydrochloride (8.30 g, 65.1 mmol) was dissolved in a mixed solvent of methanol (50 mL) and distilled water (50 mL). To the solution was added ethyl benzoylacetate (17.0 mL, 98.2 mmol) and concentrated hydrochloric acid (1.00 mL, 12.0 mmol), and the mixture was stirred at room temperature for 11 hours. The deposited solid was collected by filtration, washed (methanol) and then dried to give 3 phenyl-3-thiosemicarbazonopropionic acid ethyl ester (thiosemicarbazone) (11.1 g, 64%). distilled water (50 mL) The deposited solid was collected by filtration washed (methanol) dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thiosemicarbazide hydrochloride (8.30 g, 65.1 mmol) was dissolved in a mixed solvent of methanol (50 mL) and distilled water (50 mL). To the solution was added ethyl benzoylacetate (17.0 mL, 98.2 mmol) and concentrated hydrochloric acid (1.00 mL, 12.0 mmol), and the mixture was stirred at room temperature for 11 hours. The deposited solid was collected by filtration, washed (methanol) and then dried to give 3 phenyl-3-thiosemicarbazonopropionic acid ethyl ester (thiosemicarbazone) (11.1 g, 64%). distilled water (50 mL) The deposited solid was collected by filtration washed (methanol) dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5-hydroxyindan-1,2,3-trione, monohydrate, thiosemicarbazide hydrochloride, reflux for 2 hours.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5-methoxyindan-1,2,3-trione, monohydrate, thiosemicarbazide hydrochloride

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thiosemicarbazide hydrochloride (2.55 g, 20.0 mmol) was mixed to pyridine (20 ml), and 2,4-dichlorobenzoyl chloride (2.81 ml) was added thereto. The mixture was stirred at a room temperature for 14 hours. The solvent was distilled off. Water was added to the resulting residue, and the mixture was stirred. The precipitate was separated by filtration. 2,4-Dichlorobenzoylthiosemicarbazide (2.11 g, 8.00 mmol) obtained from the precipitate by through circulation drying was mixed to toluene (25 ml), and methanesulfonic acid (0.78 ml) was added to the mixture. The resulting mixture was heated and stirred for 6 hours. The mixture was allowed to cool to a room temperature. Then, the precipitate was separated by filtration, neutralized with water and 25% ammonia water, and stirred for 30 minutes. The precipitate was separated by filtration, washed with water, and subjected to through circulation drying to give the title compound (1.14 g, 58%) as a white substance. was added The solvent was distilled off Water was added to the resulting residue the mixture was stirred The precipitate was separated by filtration

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2-ethoxy-4-p-methoxybenzylthio-1-pyrroline (900 mg) and thiosemicarbazide hydrochloride (433 mg) in ethanol (30 ml) was refluxed under heating for 1.5 hours. The reaction solution was evaporated to dryness under reduced pressure, then the residue was distributed between ethyl acetate and 5% aqueous solution of sodium hydroxide and the organic phase was dried over Na2SO4 before the solvent was distilled off under reduced pressure. The resultant residue was passed through a column packed with 25 g of silica gel and eluted with ethyl acetate and thus 230 mg of the objective compound was obtained as colorless foam. under heating for 1.5 hours The reaction solution was evaporated to dryness under reduced pressure the organic phase was dried over Na2SO4 before the solvent was distilled off under reduced pressure eluted with ethyl acetate