methyl 4-azidobutanoate

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:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl 4-azidobutyrate (200 mg, 1.40 mmol) and 1-ethynyl-4-methoxybenzene (277 mg, 210 mmol) were dissolved in dioxane (3 mL) and heated in a microwave reactor for 5 min at 175° C. The reaction mixture was filtered and the filtrate was concentrated under vacuum. Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) and stirred at RT for 5 h. The methanol was removed under vacuum and the residue was dissolved in dioxane (5 mL) and treated with concentrated HCl dropwise until a precipitate formed. The resulting acid was collected by filtration and the purity was measured by RPLC (78%). Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid (125 mg, 0.50 mmol) and 4-(3-amino-propylamino)-2H-phthalazin-1-one (100 mg, 0.46 mmol) were dissolved in DMF (2 mL) and treated with EDC (95 mg, 0.50 mmol) and triethylamine (76 mg, 0.75 mmol). 3-[4-(4-Methoxy-phenyl)-[1,2,3]triazol-1-yl]-N-[3-(4-oxo-3,4-dihydro-phthalazin-1-ylamino)-propyl]-propionamide was isolated by preparative RPLC. The reaction mixture was filtered the filtrate was concentrated under vacuum Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) The methanol was removed under vacuum the residue was dissolved in dioxane (5 mL) treated with concentrated HCl dropwise until a precipitate formed The resulting acid was collected by filtration

反応条件: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl 4-azidobutyrate (200 mg, 1.40 mmol) and 1-ethynyl-4-methoxybenzene (277 mg, 210 mmol) were dissolved in dioxane (3 mL) and heated in a microwave reactor for 5 min at 175° C. The reaction mixture was filtered and the filtrate was concentrated under vacuum. Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) and stirred at RT for 5 h. The methanol was removed under vacuum and the residue was dissolved in dioxane (5 mL) and treated with concentrated HCl dropwise until a precipitate formed. The resulting acid was collected by filtration and the purity was measured by RPLC (78%). Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid (125 mg, 0.50 mmol) and 4-(3-amino-propylamino)-2H-phthalazin-1-one (100 mg, 0.46 mmol) were dissolved in DMF (2 mL) and treated with EDC (95 mg, 0.50 mmol) and triethylamine (76 mg, 0.75 mmol). 3-[4-(4-Methoxy-phenyl)-[1,2,3]triazol-1-yl]-N-[3-(4-oxo-3,4-dihydro-phthalazin-1-ylamino)-propyl]-propionamide was isolated by preparative RPLC. The reaction mixture was filtered the filtrate was concentrated under vacuum Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) The methanol was removed under vacuum the residue was dissolved in dioxane (5 mL) treated with concentrated HCl dropwise until a precipitate formed The resulting acid was collected by filtration

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: Methyl 4-azidobutanoate was suspended in 1N NaOH (1.2 eq) and the minimum of MeOH was added to make the reaction mixture homogenous. After 1 h at RT temperature, MeOH was removed in vacuo. The aqueous solution After 1 h at RT temperature, MeOH was removed in vacuo

反応条件: temp:47.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl-4-bromobutyrate in DMSO (0.6 M) was added with stirring NaN3 (1.5 eq). The suspension was heated (45-50° C., oil bath) with stirring for 5 h. After cooling, H2O was added and the mixture extracted with Et2O. The organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the crude oil used without further purification (99%). After cooling the mixture extracted with Et2O The organic extracts were washed with brine dried over Na2SO4 The solvent was removed in vacuo the crude oil used without further purification (99%)

反応条件: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl 4-azidobutyrate (200 mg, 1.40 mmol) and 1-ethynyl-4-methoxybenzene (277 mg, 210 mmol) were dissolved in dioxane (3 mL) and heated in a microwave reactor for 5 min at 175° C. The reaction mixture was filtered and the filtrate was concentrated under vacuum. Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) and stirred at RT for 5 h. The methanol was removed under vacuum and the residue was dissolved in dioxane (5 mL) and treated with concentrated HCl dropwise until a precipitate formed. The resulting acid was collected by filtration and the purity was measured by RPLC (78%). Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid (125 mg, 0.50 mmol) and 4-(3-amino-propylamino)-2H-phthalazin-1-one (100 mg, 0.46 mmol) were dissolved in DMF (2 mL) and treated with EDC (95 mg, 0.50 mmol) and triethylamine (76 mg, 0.75 mmol). 3-[4-(4-Methoxy-phenyl)-[1,2,3]triazol-1-yl]-N-[3-(4-oxo-3,4-dihydro-phthalazin-1-ylamino)-propyl]-propionamide was isolated by preparative RPLC. The reaction mixture was filtered the filtrate was concentrated under vacuum Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) The methanol was removed under vacuum the residue was dissolved in dioxane (5 mL) treated with concentrated HCl dropwise until a precipitate formed The resulting acid was collected by filtration

反応条件: temp:0.00; pressure:0.00; stir: