2-[2-(methylamino)ethyl]isoindole-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the HCl salt of 2-(2-Methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added quinoline-2-carbaldehyde(1.2 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (1.2 eq) at rt.; the solution was allowed to stir for 16 hours. After concentration, the solution was diluted with ethyl acetate, washed with NaHCO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated and pumped on. The yellow oil was then purified using flash chromatography (2% methanol/dichloromethane with 0.1% triethylamine) to yield 2-[2-(Methyl-quinolin-2-ylmethyl-amino)-ethyl]-isoindole-1,3-dione as a green solid. MH+(346). After concentration the solution was diluted with ethyl acetate washed with NaHCO3(sat), NaCl(sat) dried over MgSO4 filtered concentrated The yellow oil was then purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added nicotinaldehyde (1.5 eq), sodium acetoborohydride (4.5 eq) and acetic acid (1.5 eq). After stirring at room temperature for 1 hour, NaHCO3(sat) was added to the reaction mixture followed by an extraction with dichloromethane. The organic phase was washed with H2O, NaCl(sat) (50 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA (2L) to yield 2-[2-methyl-pyridin-3-ylmethyl-amino)-ethyl]-isoindole-1,3-dione (57%). MH+(296). followed by an extraction with dichloromethane The organic phase was washed with H2O, NaCl(sat) (50 mL) dried over sodium sulfate filtered concentrated The crude product was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the HCl salt of 2-(2-Methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added quinoline-2-carbaldehyde(1.2 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (1.2 eq) at rt.; the solution was allowed to stir for 16 hours. After concentration, the solution was diluted with ethyl acetate, washed with NaHCO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated and pumped on. The yellow oil was then purified using flash chromatography (2% methanol/dichloromethane with 0.1% triethylamine) to yield 2-[2-(Methyl-quinolin-2-ylmethyl-amino)-ethyl]-isoindole-1,3-dione as a green solid. MH+(346). After concentration the solution was diluted with ethyl acetate washed with NaHCO3(sat), NaCl(sat) dried over MgSO4 filtered concentrated The yellow oil was then purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the HCl salt of 2-(2-Methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added quinoline-2-carbaldehyde(1.2 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (1.2 eq) at rt.; the solution was allowed to stir for 16 hours. After concentration, the solution was diluted with ethyl acetate, washed with NaHCO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated and pumped on. The yellow oil was then purified using flash chromatography (2% methanol/dichloromethane with 0.1% triethylamine) to yield 2-[2-(Methyl-quinolin-2-ylmethyl-amino)-ethyl]-isoindole-1,3-dione as a green solid. MH+(346). After concentration the solution was diluted with ethyl acetate washed with NaHCO3(sat), NaCl(sat) dried over MgSO4 filtered concentrated The yellow oil was then purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added nicotinaldehyde (1.5 eq), sodium acetoborohydride (4.5 eq) and acetic acid (1.5 eq). After stirring at room temperature for 1 hour, NaHCO3(sat) was added to the reaction mixture followed by an extraction with dichloromethane. The organic phase was washed with H2O, NaCl(sat) (50 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA (2L) to yield 2-[2-methyl-pyridin-3-ylmethyl-amino)-ethyl]-isoindole-1,3-dione (57%). MH+(296). followed by an extraction with dichloromethane The organic phase was washed with H2O, NaCl(sat) (50 mL) dried over sodium sulfate filtered concentrated The crude product was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the HCl salt of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added quinoline-2-carbaldehyde (1.2 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (1.2 eq) at room temperature. The solution was allowed to stir for 16 hours. After concentration, the solution was diluted with ethyl acetate, washed with NaHCO3 (sat.), NaCl (sat.). dried over MgSO4 filtered, concentrated, and pumped on. The yellow oil was then purified using flash chromatography (2% methanol/dichloromethane with 0.1% triethylamine) to yield 2-[2-(methyl-quinolin-2-ylmethyl-amino)-ethyl]-isoindole-1,3-dione as a green solid. MH+(346) After concentration the solution was diluted with ethyl acetate washed with NaHCO3 (sat.), NaCl (sat.) dried over MgSO4 filtered concentrated The yellow oil was then purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added nicotinaldehyde (1.5 eq), sodium acetoborohydride (4.5 eq) and acetic acid (1.5 eq). After stirring at room temperature for 1 h, NaHCO3 (sat.) was added to the reaction mixture followed by an extraction with dichloromethane. The organic phase was washed with H2O, NaCl (sat.) (50 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA (2L) to yield 2-[2-methyl-pyridin-3-ylmethyl-amino)-ethyl]-isoindole-1,3-dione (57%). MH+(296) followed by an extraction with dichloromethane The organic phase was washed with H2O, NaCl (sat.) (50 ml) dried over sodium sulfate filtered concentrated The crude product was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the HCl salt of 2-(2-Methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added quinoline-2-carbaldehyde(1.2 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (1.2 eq) at rt.; the solution was allowed to stir for 16 hours. After concentration, the solution was diluted with ethyl acetate, washed with NaHCO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated and pumped on. The yellow oil was then purified using flash chromatography (2% methanol/dichloromethane with 0.1% triethylamine) to yield 2-[2-(Methyl-quinolin-2-ylmethyl-amino)-ethyl]-isoindole-1,3-dione as a green solid. MH+(346). After concentration the solution was diluted with ethyl acetate washed with NaHCO3(sat), NaCl(sat) dried over MgSO4 filtered concentrated The yellow oil was then purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added nicotinaldehyde (1.5 eq), sodium acetoborohydride (4.5 eq) and acetic acid (1.5 eq). After stirring at room temperature for 1 hour, NaHCO3(sat) was added to the reaction mixture followed by an extraction with dichloromethane. The organic phase was washed with H2O, NaCl(sat) (50 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA (2L) to yield 2-[2-methyl-pyridin-3-ylmethyl-amino)-ethyl]-isoindole-1,3-dione (57%). MH+(296). followed by an extraction with dichloromethane The organic phase was washed with H2O, NaCl(sat) (50 mL) dried over sodium sulfate filtered concentrated The crude product was purified by flash chromatography