isothiocyanatocyclopropane

反応条件: temp:0.00; pressure:0.00; stir:

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: 4,5-Dichloro-1,2-phenylenediamine (6.04 g, 34.1 mmol), cyclopropyl isothiocyanate (3.69 g, 37.2 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (20.1 g, 47.4 mmol) and pyridine (135 mL) were used according to general procedure I. The product was recrystallized from acetonitrile to afford 5.82 g (70%) of a yellow solid; m.p. 223-225° C. Anal. Calcd for C10H9Cl2N3: C, 49.61; H, 3.75; N, 17.36. Found: C, 49.53; H, 3.78; N, 17.12. The product was recrystallized from acetonitrile

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At 0° C., cyclopropylisothiocyanate (0.32 ml) was added to a solution of N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester (410 mg, 1.6 mmol) in dichloromethane (4 ml). The reaction mixture was first stirred at 0° C. for 10 min, and successively for 2.5 h at room temperature. The solvent were removed in vacuo. The crude product was purified by flash chromatography on silica (50 g) using ethyl acetate/heptane as eluent to give 492 mg of N-((1R)1-benzyl-2-(3-cyclopropylthioureido)ethyl)-N-methylcarbamic acid tert-butylester. successively for 2.5 h at room temperature The solvent were removed in vacuo The crude product was purified by flash chromatography on silica (50 g)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a slurry of thiophene-2-carboxylic acid hydrazide (866 mg, 6.09 mmol) in iPrOH (25 ml) was added isothiocyanato-cyclopropane (602 mg, 6.08 mmol). The mixture was stirred at 70° C. for 72 h and then cooled to room temperature. The white precipitate was filtered off and suspended in a MeOH:H2O (9:1, 40 ml) together with aq. NaOH (2%, 5 ml). The reaction mixture was stirred at 70° C. overnight and then cooled to room temperature. The pH was adjusted to around 4 with aq. HCl (1N). The formed white precipitate was filtered off, washed with water and dried under vacuum (829 mg, 61%). 1H NMR (CD3OD), δ (ppm): 7.67 (dd, 1H), 7.63 (dd, 1H), 7.17 (dd, 1H), 3.15 (m, 1H), 1.14 (m, 2H), 0.86 (m, 2H). cooled to room temperature The white precipitate was filtered off The reaction mixture was stirred at 70° C. overnight cooled to room temperature The formed white precipitate was filtered off washed with water dried under vacuum (829 mg, 61%)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a slurry of thiophene-2-carboxylic acid hydrazide (866 mg, 6.09 mmol) in iPrOH (25 ml) was added isothiocyanato-cyclopropane (602 mg, 6.08 mmol). The mixture was stirred at 70° C. for 72 h and then cooled to room temperature. The white precipitate was filtered off and suspended in a MeOH:H2O (9:1, 40 ml) together with aq. NaOH (2%, 5 ml). The reaction mixture was stirred at 70° C. overnight and then cooled to room temperature. The pH was adjusted to around 4 with aq. HCl (1N). The formed white precipitate was filtered off, washed with water and dried under vacuum (829 mg, 61%). 1H NMR (CD3OD), δ (ppm): 7.67 (dd, 1H), 7.63 (dd, 1H), 7.17 (dd, 1H), 3.15 (m, 1H), 1.14 (m, 2H), 0.86 (m, 2H). cooled to room temperature The white precipitate was filtered off The reaction mixture was stirred at 70° C. overnight cooled to room temperature The formed white precipitate was filtered off washed with water dried under vacuum (829 mg, 61%)

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

実験手順: Cyclopropyl isothiocyanate (650 mg, 6.6 mmol) was added to 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]-N-methylmethanamine (1.47 g, 6.5 mmol) in EtOH (20 mL). After 3 h the formed precipitate was filtrated off and washed with cold EtOH to give 1.63 g (78%) of the title compound. LC-MS (M++1): 323. After 3 h the formed precipitate was filtrated off washed with cold EtOH

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

実験手順: Cyclopropyl isothiocyanate (650 mg, 6.6 mmol) was added to 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]-N-methylmethanamine (1.47 g, 6.5 mmol) in EtOH (20 mL). After 3 h the formed precipitate was filtrated off and washed with cold EtOH to give 1.63 g (78%) of the title compound. LC-MS (M++1): 323. After 3 h the formed precipitate was filtrated off washed with cold EtOH

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a slurry of thiophene-2-carboxylic acid hydrazide (866 mg, 6.09 mmol) in iPrOH (25 ml) was added isothiocyanato-cyclopropane (602 mg, 6.08 mmol). The mixture was stirred at 70° C. for 72 h and then cooled to room temperature. The white precipitate was filtered off and suspended in a MeOH:H2O (9:1, 40 ml) together with aq. NaOH (2%, 5 ml). The reaction mixture was stirred at 70° C. overnight and then cooled to room temperature. The pH was adjusted to around 4 with aq. HCl (1N). The formed white precipitate was filtered off, washed with water and dried under vacuum (829 mg, 61%). 1H NMR (CD3OD), δ (ppm): 7.67 (dd, 1H), 7.63 (dd, 1H), 7.17 (dd, 1H), 3.15 (m, 1H), 1.14 (m, 2H), 0.86 (m, 2H). cooled to room temperature The white precipitate was filtered off The reaction mixture was stirred at 70° C. overnight cooled to room temperature The formed white precipitate was filtered off washed with water dried under vacuum (829 mg, 61%)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a slurry of thiophene-2-carboxylic acid hydrazide (866 mg, 6.09 mmol) in iPrOH (25 ml) was added isothiocyanato-cyclopropane (602 mg, 6.08 mmol). The mixture was stirred at 70° C. for 72 h and then cooled to room temperature. The white precipitate was filtered off and suspended in a MeOH:H2O (9:1, 40 ml) together with aq. NaOH (2%, 5 ml). The reaction mixture was stirred at 70° C. overnight and then cooled to room temperature. The pH was adjusted to around 4 with aq. HCl (1N). The formed white precipitate was filtered off, washed with water and dried under vacuum (829 mg, 61%). 1H NMR (CD3OD), δ (ppm): 7.67 (dd, 1H), 7.63 (dd, 1H), 7.17 (dd, 1H), 3.15 (m, 1H), 1.14 (m, 2H), 0.86 (m, 2H). cooled to room temperature The white precipitate was filtered off The reaction mixture was stirred at 70° C. overnight cooled to room temperature The formed white precipitate was filtered off washed with water dried under vacuum (829 mg, 61%)

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

実験手順: (6-Chloro-4,5-dimethylpyridazin-3-yl)hydrazine (W3.006, 540 mg) was dissolved in methylene chloride (50 ml), and cyclopropyl isothiocyanate (290 μl) was added while stirring. The mixture was stirred at RT for 7 h and then left to stand overnight. Thereafter, it was admixed with diethyl ether (50 ml) and stirred for 3 h, and the precipitate formed was filtered off with suction. The precipitate was washed with ether and dried under reduced pressure. 830 mg of the title compound were obtained. The mixture was stirred at RT for 7 h left stirred for 3 h the precipitate formed was filtered off with suction The precipitate was washed with ether dried under reduced pressure

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

実験手順: 4,5-Dichloro-1,2-phenylenediamine (6.04 g, 34.1 mmol), cyclopropyl isothiocyanate (3.69 g, 37.2 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (20.1 g, 47.4 mmol) and pyridine (135 mL) were used according to general procedure I. The product was recrystallized from acetonitrile to afford 5.82 g (70%) of a yellow solid; m.p. 223-225° C. Anal. Calcd for C10H9Cl2N3 : C, 49.61; H, 3.75; N, 17.36. Found: C, 49.53; H, 3.78; N, 17.12. The product was recrystallized from acetonitrile