1-Piperazinecarboxamide,N-(1-methylethyl)-(9CI)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 6-bromopicolinaldehyde (5, 1.00 g, 5.38 mmol) and N-isopropylpiperazine-1-carboxamide (4, 1.10 g, 6.45 mmol) in N,N-dimethylacetamide (20 mL) was treated with K2CO3 (2.23 g, 16.1 mmol) and heated at 80° C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH to afford the title compound (0.35 g, 24%) as an impure yellow solid: Multimode MS m/z 172 [M+H]+. The mixture was cooled to room temperature concentrated The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 6-bromopicolinaldehyde (5, 1.00 g, 5.38 mmol) and N-isopropylpiperazine-1-carboxamide (4, 1.10 g, 6.45 mmol) in N,N-dimethylacetamide (20 mL) was treated with K2CO3 (2.23 g, 16.1 mmol) and heated at 80° C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH to afford the title compound (0.35 g, 24%) as an impure yellow solid: Multimode MS m/z 172 [M+H]+. The mixture was cooled to room temperature concentrated The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH

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

实验步骤: To a solution of benzyl 4-(isopropylcarbamoyl)piperazine-1-carboxylate (3, 3.94 g, 12.9 mmol) in methanol (100 mL) was added 10% Pd/C (50% wet, 0.400 g) and the mixture was stirred under 1 atmosphere of hydrogen for 16 h. After this time, the mixture was filtered through Celite and the filtrate concentrated to afford the title compound (2.88 g, >99%): 1H NMR (300 MHz, CD3OD) δ 4.00-3.80 (m, 1H), 3.45-3.35 (m, 4H), 2.88-2.78 (m, 4H), 1.13 (d, J=6.5 Hz, 6H); Multimode MS m/z 172 [M+H]+. After this time, the mixture was filtered through Celite the filtrate concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 6-bromopicolinaldehyde (5, 1.00 g, 5.38 mmol) and N-isopropylpiperazine-1-carboxamide (4, 1.10 g, 6.45 mmol) in N,N-dimethylacetamide (20 mL) was treated with K2CO3 (2.23 g, 16.1 mmol) and heated at 80° C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH to afford the title compound (0.35 g, 24%) as an impure yellow solid: Multimode MS m/z 172 [M+H]+. The mixture was cooled to room temperature concentrated The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH

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

实验步骤: To a solution of benzyl 4-(isopropylcarbamoyl)piperazine-1-carboxylate (3, 3.94 g, 12.9 mmol) in methanol (100 mL) was added 10% Pd/C (50% wet, 0.400 g) and the mixture was stirred under 1 atmosphere of hydrogen for 16 h. After this time, the mixture was filtered through Celite and the filtrate concentrated to afford the title compound (2.88 g, >99%): 1H NMR (300 MHz, CD3OD) δ 4.00-3.80 (m, 1H), 3.45-3.35 (m, 4H), 2.88-2.78 (m, 4H), 1.13 (d, J=6.5 Hz, 6H); Multimode MS m/z 172 [M+H]+. After this time, the mixture was filtered through Celite the filtrate concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 6-bromopicolinaldehyde (5, 1.00 g, 5.38 mmol) and N-isopropylpiperazine-1-carboxamide (4, 1.10 g, 6.45 mmol) in N,N-dimethylacetamide (20 mL) was treated with K2CO3 (2.23 g, 16.1 mmol) and heated at 80° C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH to afford the title compound (0.35 g, 24%) as an impure yellow solid: Multimode MS m/z 172 [M+H]+. The mixture was cooled to room temperature concentrated The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH

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

实验步骤: To a solution of benzyl 4-(isopropylcarbamoyl)piperazine-1-carboxylate (3, 3.94 g, 12.9 mmol) in methanol (100 mL) was added 10% Pd/C (50% wet, 0.400 g) and the mixture was stirred under 1 atmosphere of hydrogen for 16 h. After this time, the mixture was filtered through Celite and the filtrate concentrated to afford the title compound (2.88 g, >99%): 1H NMR (300 MHz, CD3OD) δ 4.00-3.80 (m, 1H), 3.45-3.35 (m, 4H), 2.88-2.78 (m, 4H), 1.13 (d, J=6.5 Hz, 6H); Multimode MS m/z 172 [M+H]+. After this time, the mixture was filtered through Celite the filtrate concentrated