(3R)-N,N-dimethylpiperidine-3-carboxamide

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-chloro-3-nitropyridin-2-amine (4.15 g, 24.0 mmol) in N,N-dimethylformamide (41 mL) was added (R)—N,N-dimethylpiperidine-3-carboxamide (3.74 g, 2.40 mmol) followed by triethylamine (10.7 mL, 64.800 mmol). The reaction mixture was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via column chromatography to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide. The solvent was removed under reduced pressure the residue was purified via column chromatography

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-chloro-3-nitropyridin-2-amine (4.15 g, 24.0 mmol) in N,N-dimethylformamide (41 mL) was added (R)—N,N-dimethylpiperidine-3-carboxamide (3.74 g, 2.40 mmol) followed by triethylamine (10.7 mL, 64.800 mmol). The reaction mixture was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via column chromatography to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide. The solvent was removed under reduced pressure the residue was purified via column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (R)—N,N-dimethylpiperidine-3-carboxamide (10 g, 64.04 mmol) in dimethylsulfoxide (100 mL) were added triethylamine (17.8 mL, 128.08 mmol) and 6-chloro-3-nitropyridin-2-amine (7.76 g, 44.82 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 110° C. for 16 h. The reaction mixture was added to cold water and extracted with ethyl acetate. The organic layer was washed with cold water 3 times, dried over sodium sulfate and evaporated under reduced pressure. The crude compound was purified via flash chromatography and then treated with 1:1 petroleum ether and diethyl ether to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide (11 g, 72%). MS (ES+APCI) (M+H) 294.1; LCMS retention time: 2.777 min (Method E1) extracted with ethyl acetate The organic layer was washed with cold water 3 times dried over sodium sulfate evaporated under reduced pressure The crude compound was purified via flash chromatography treated with 1:1 petroleum ether and diethyl ether

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-chloro-3-nitropyridin-2-amine (4.15 g, 24.0 mmol) in N,N-dimethylformamide (41 mL) was added (R)—N,N-dimethylpiperidine-3-carboxamide (3.74 g, 2.40 mmol) followed by triethylamine (10.7 mL, 64.800 mmol). The reaction mixture was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via column chromatography to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide. The solvent was removed under reduced pressure the residue was purified via column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (R)—N,N-dimethylpiperidine-3-carboxamide (10 g, 64.04 mmol) in dimethylsulfoxide (100 mL) were added triethylamine (17.8 mL, 128.08 mmol) and 6-chloro-3-nitropyridin-2-amine (7.76 g, 44.82 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 110° C. for 16 h. The reaction mixture was added to cold water and extracted with ethyl acetate. The organic layer was washed with cold water 3 times, dried over sodium sulfate and evaporated under reduced pressure. The crude compound was purified via flash chromatography and then treated with 1:1 petroleum ether and diethyl ether to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide (11 g, 72%). MS (ES+APCI) (M+H) 294.1; LCMS retention time: 2.777 min (Method E1) extracted with ethyl acetate The organic layer was washed with cold water 3 times dried over sodium sulfate evaporated under reduced pressure The crude compound was purified via flash chromatography treated with 1:1 petroleum ether and diethyl ether