N-环丙基苯-1,2-二胺

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

实验步骤: To a solution of N1-cyclopropylbenzene-1,2-diamine (221 mg, 1.49 mmol) and triethylamine (0.3 mL, 2.2 mmol) in DMF was added a solution of methyl 8-chloro-8-oxooctanoate (260 mg, 1.3 mmol) in DMF at 0° C. drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated to give crude methyl 8-(2-(cyclopropylamino)phenylamino)-8-oxooctanoate (390 mg) washed with 1 N HCl, saturated sodium bicarbonate solution and brine The separated organic layer was concentrated

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

实验步骤: To a solution of N-cyclopropyl-2-nitroaniline (365 mg, 2.05 mmol) and ammonium formate (516 mg, 8.2 mmol) in methanol was added catalytic amount of palladium on carbon (5%). The mixture was heated to reflux under a nitrogen atmosphere overnight and filtered. The filtrate was concentrated and purified by biotage column chromatography to give N1-cyclopropylbenzene-1,2-diamine (296 mg) The mixture was heated to reflux under a nitrogen atmosphere overnight filtered The filtrate was concentrated purified by biotage column chromatography

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

实验步骤: To a solution of N-cyclopropyl-2-nitroaniline (365 mg, 2.05 mmol) and ammonium formate (516 mg, 8.2 mmol) in methanol was added catalytic amount of palladium on carbon (5%). The mixture was heated to reflux under a nitrogen atmosphere overnight and filtered. The filtrate was concentrated and purified by biotage column chromatography to give N1-cyclopropylbenzene-1,2-diamine (296 mg) The mixture was heated to reflux under a nitrogen atmosphere overnight filtered The filtrate was concentrated purified by biotage column chromatography

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

实验步骤: To a solution of N1-cyclopropylbenzene-1,2-diamine (221 mg, 1.49 mmol) and triethylamine (0.3 mL, 2.2 mmol) in DMF was added a solution of methyl 8-chloro-8-oxooctanoate (260 mg, 1.3 mmol) in DMF at 0° C. drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated to give crude methyl 8-(2-(cyclopropylamino)phenylamino)-8-oxooctanoate (390 mg) washed with 1 N HCl, saturated sodium bicarbonate solution and brine The separated organic layer was concentrated

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

实验步骤: To a solution of N1-cyclopropylbenzene-1,2-diamine (221 mg, 1.49 mmol) and triethylamine (0.3 mL, 2.2 mmol) in DMF was added a solution of methyl 8-chloro-8-oxooctanoate (260 mg, 1.3 mmol) in DMF at 0° C. drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated to give crude methyl 8-(2-(cyclopropylamino)phenylamino)-8-oxooctanoate (390 mg) washed with 1 N HCl, saturated sodium bicarbonate solution and brine The separated organic layer was concentrated

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

实验步骤: To a solution of N-cyclopropyl-2-nitroaniline (365 mg, 2.05 mmol) and ammonium formate (516 mg, 8.2 mmol) in methanol was added catalytic amount of palladium on carbon (5%). The mixture was heated to reflux under a nitrogen atmosphere overnight and filtered. The filtrate was concentrated and purified by biotage column chromatography to give N1-cyclopropylbenzene-1,2-diamine (296 mg) The mixture was heated to reflux under a nitrogen atmosphere overnight filtered The filtrate was concentrated purified by biotage column chromatography

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

实验步骤: To a solution of title compound 381 (0.83 g, 5.84 mmol) and diisopropylethylamine (1.02 mL, 0.74 mmol) in THF (50 mL) was added a solution of 2-chloronicotinoyl chloride (1.03 g, 5.84 mmol) in THF at 0° C. The reaction mixture was stirred over night and concentrated. To the residue was added a saturated solution of bicarbonate (3 mL) and this aqueous layer was extracted with DCM (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The solid was triturated in DCM (3 mL) and filtered. The filtrate was evaporated and purified by flash chromatography (0% to 80% ethyl acetate in hexanes). The 2 solids were mixed to afford title compound 382 (1.1 g, 65%) as a white solid. MS (m/z): 288.0 (M+H). concentrated To the residue was added a saturated solution of bicarbonate (3 mL) this aqueous layer was extracted with DCM (2×) The combined organic layers were washed with brine dried over sodium sulfate filtered evaporated The solid was triturated in DCM (3 mL) filtered The filtrate was evaporated purified by flash chromatography (0% to 80% ethyl acetate in hexanes) The 2 solids were mixed

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

实验步骤: To a solution of title compound 381 (0.83 g, 5.84 mmol) and diisopropylethylamine (1.02 mL, 0.74 mmol) in THF (50 mL) was added a solution of 2-chloronicotinoyl chloride (1.03 g, 5.84 mmol) in THF at 0° C. The reaction mixture was stirred over night and concentrated. To the residue was added a saturated solution of bicarbonate (3 mL) and this aqueous layer was extracted with DCM (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The solid was triturated in DCM (3 mL) and filtered. The filtrate was evaporated and purified by flash chromatography (0% to 80% ethyl acetate in hexanes). The 2 solids were mixed to afford title compound 382 (1.1 g, 65%) as a white solid. MS (m/z): 288.0 (M+H). concentrated To the residue was added a saturated solution of bicarbonate (3 mL) this aqueous layer was extracted with DCM (2×) The combined organic layers were washed with brine dried over sodium sulfate filtered evaporated The solid was triturated in DCM (3 mL) filtered The filtrate was evaporated purified by flash chromatography (0% to 80% ethyl acetate in hexanes) The 2 solids were mixed

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

实验步骤: Title compound 380 (3.1 g, 17.4 mmol) and palladium on charcoal 10% (0.3 g, 10% w/w) were mixed in ethanol (100 mL) and the reaction mixture was stirred under 45 PSI of hydrogen for 4 hours. The mixture was filtered to remove the catalyst and the filtrate was evaporated to afford title compound 381 as black oil that was used without further purification. MS (m/z): 148.9 (M+H). The mixture was filtered to remove the catalyst the filtrate was evaporated

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

实验步骤: A solution of 1.71 g (0.0115 mole) of N-cyclopropyl-1,2-phenylenediamine and 2.12 ml (0.0115 mole) of triethylorthoacetate in 50 ml of ethyl acetate was heated to reflux for 2 hours. The solvent was removed and the residue partitioned between chloroform and water. The organic phase was separated, dried over sodium sulfate and concentrated to give 1.87 g of a brown oil. to reflux for 2 hours The solvent was removed the residue partitioned between chloroform and water The organic phase was separated dried over sodium sulfate concentrated

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

实验步骤: A solution of 1.71 g (0.0115 mole) of N-cyclopropyl-1,2-phenylenediamine and 2.12 ml (0.0115 mole) of triethylorthoacetate in 50 ml of ethyl acetate was heated to reflux for 2 hours. The solvent was removed and the residue partitioned between chloroform and water. The organic phase was separated, dried over sodium sulfate and concentrated to give 1.87 g of a brown oil. to reflux for 2 hours The solvent was removed the residue partitioned between chloroform and water The organic phase was separated dried over sodium sulfate concentrated

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

实验步骤: To a solution of N1-cyclopropylbenzene-1,2-diamine (221 mg, 1.49 mmol) and triethylamine (0.3 mL, 2.2 mmol) in DMF was added a solution of methyl 8-chloro-8-oxooctanoate (260 mg, 1.3 mmol) in DMF at 0° C. drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated to give crude methyl 8-(2-(cyclopropylamino)phenylamino)-8-oxooctanoate (390 mg) washed with 1 N HCl, saturated sodium bicarbonate solution and brine The separated organic layer was concentrated