苄基 N-[(3Z)-3-(丙-2-基肼基亚基)丙基]氨基甲酸酯

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

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (0.5 g, 1.9 mmol) and 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (0.48 g, 1.9 mmol) in pyridine (20 mL) was stirred at rt for 2 days. The mixture was cooled to rt, concentrated, and the residue purified by FCC to give the title compound. concentrated the residue purified by FCC

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

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (1.0 mg, 3.8 mmol), 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (0.96 mg, 3.8 mmol), and Et3N (1.53 g, 15.2 mmol) in THF (40 mL) was stirred at 60° C. for 3 days. The mixture was cooled to rt, concentrated, and the residue purified by FCC to give the title compound. concentrated the residue purified by FCC

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

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (1.0 mg, 3.8 mmol), 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (0.96 mg, 3.8 mmol), and Et3N (1.53 g, 15.2 mmol) in THF (40 mL) was stirred at 60° C. for 3 days. The mixture was cooled to rt, concentrated, and the residue purified by FCC to give the title compound. concentrated the residue purified by FCC

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (60.0 mg, 0.228 mmol) and 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (54.0 mg, 0.213 mmol) in THF (2 mL) was stirred at rt for 3 days. The mixture was treated with additional [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (1.4 equiv.) and was stirred at 60° C. for 18 h. Additional [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (2.1 equiv.) was added, and the mixture was stirred at 60° C. for 18 h. The mixture was concentrated to oil and the residue was purified by FCC to give the title compound. the mixture was stirred at 60° C. for 18 h The mixture was concentrated to oil the residue was purified by FCC

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

实验步骤: To a stirred solution of isopropylhydrazine hydrochloride (92.4 g, 0.84 mol) and (3-oxo-propyl)-carbamic acid benzyl ester (173 g, 0.84 mol) in isopropyl alcohol (1.7 L) was added Et3N (140 mL, 1.0 mol) over 20 min. The resulting slurry was heated at reflux for 3 h, and then was cooled to rt and concentrated. The residue was partitioned between EtOAc (700 mL) and water (700 mL). The organic layer was washed with water (3×500 mL), satd. aq. NaCl (300 mL), dried (MgSO4), and concentrated to afford the title compound. The crude product was used in next reaction without purification. MS (ESI): exact mass calcd. for C14H21N3O2, 263.16; m/z found, 264.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.36-7.25 (m, 5H), 7.02 (t, J=4.5, 1H), 5.10 (br s, 1H), 5.09 (s, 2H), 3.45-3.34 (m, 3H), 2.40-2.34 (m, 2H), 1.11 (d, J=6.4, 6H). The resulting slurry was heated at reflux for 3 h concentrated The residue was partitioned between EtOAc (700 mL) and water (700 mL) The organic layer was washed with water (3×500 mL) aq. NaCl (300 mL), dried (MgSO4) concentrated

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

实验步骤: To a stirred solution of isopropylhydrazine hydrochloride (92.4 g, 0.84 mol) and (3-oxo-propyl)-carbamic acid benzyl ester (173 g, 0.84 mol) in isopropyl alcohol (1.7 L) was added Et3N (140 mL, 1.0 mol) over 20 min. The resulting slurry was heated at reflux for 3 h, and then was cooled to rt and concentrated. The residue was partitioned between EtOAc (700 mL) and water (700 mL). The organic layer was washed with water (3×500 mL), satd. aq. NaCl (300 mL), dried (MgSO4), and concentrated to afford the title compound. The crude product was used in next reaction without purification. MS (ESI): exact mass calcd. for C14H21N3O2, 263.16; m/z found, 264.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.36-7.25 (m, 5H), 7.02 (t, J=4.5, 1H), 5.10 (br s, 1H), 5.09 (s, 2H), 3.45-3.34 (m, 3H), 2.40-2.34 (m, 2H), 1.11 (d, J=6.4, 6H). The resulting slurry was heated at reflux for 3 h concentrated The residue was partitioned between EtOAc (700 mL) and water (700 mL) The organic layer was washed with water (3×500 mL) aq. NaCl (300 mL), dried (MgSO4) concentrated

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

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (0.5 g, 1.9 mmol) and 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (0.48 g, 1.9 mmol) in pyridine (20 mL) was stirred at rt for 2 days. The mixture was cooled to rt, concentrated, and the residue purified by FCC to give the title compound. concentrated the residue purified by FCC

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

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (1.0 mg, 3.8 mmol), 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (0.96 mg, 3.8 mmol), and Et3N (1.53 g, 15.2 mmol) in THF (40 mL) was stirred at 60° C. for 3 days. The mixture was cooled to rt, concentrated, and the residue purified by FCC to give the title compound. concentrated the residue purified by FCC

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (60.0 mg, 0.228 mmol) and 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (54.0 mg, 0.213 mmol) in THF (2 mL) was stirred at rt for 3 days. The mixture was treated with additional [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (1.4 equiv.) and was stirred at 60° C. for 18 h. Additional [3-(isopropyl-hydrazono)-propyl]-carbamic acid benzyl ester (2.1 equiv.) was added, and the mixture was stirred at 60° C. for 18 h. The mixture was concentrated to oil and the residue was purified by FCC to give the title compound. the mixture was stirred at 60° C. for 18 h The mixture was concentrated to oil the residue was purified by FCC

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

实验步骤: To a stirred solution of isopropylhydrazine hydrochloride (92.4 g, 0.84 mol) and (3-oxo-propyl)-carbamic acid benzyl ester (173 g, 0.84 mol) in isopropyl alcohol (1.7 L) was added Et3N (140 mL, 1.0 mol) over 20 min. The resulting slurry was heated at reflux for 3 h, and then was cooled to rt and concentrated. The residue was partitioned between EtOAc (700 mL) and water (700 mL). The organic layer was washed with water (3×500 mL), satd. aq. NaCl (300 mL), dried (MgSO4), and concentrated to afford the title compound. The crude product was used in next reaction without purification. MS (ESI): exact mass calcd. for C14H21N3O2, 263.16; m/z found, 264.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.36-7.25 (m, 5H), 7.02 (t, J=4.5, 1H), 5.10 (br s, 1H), 5.09 (s, 2H), 3.45-3.34 (m, 3H), 2.40-2.34 (m, 2H), 1.11 (d, J=6.4, 6H). The resulting slurry was heated at reflux for 3 h concentrated The residue was partitioned between EtOAc (700 mL) and water (700 mL) The organic layer was washed with water (3×500 mL) aq. NaCl (300 mL), dried (MgSO4) concentrated