3-methyl-2-piperidin-1-ylaniline

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

実験手順: Using a procedure similar to example 3, step (d), 3-methyl-2-piperidin-1-yl-phenylamine (68 mg, 0.35 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (65 mg, 0.42 mmol) in the presence of DIEA (134 μL, 0.77 mmol) to afford 13 mg (12%) of the title compound as a waxy yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 10.7 (br s, 1H), 8.33 (d, 1H, J=8.0 Hz), 7.27 (d, 1H, J=3.7 Hz), 7.22 (dd, 1H, 3.7 Hz), 7.12 (t, 1H, J=7.9 Hz), 6.87 (dd, 1H, J=0.7, 7.7 Hz), 3.22-3.28 (m, 2H), 2.88-2.91 (m, 1H), 2.41 (s, 3H), 2.01-2.04 (m, 1H), 1.80-1.86 (m, 4H), 1.43-1.47 (m, 1H); Mass spectrum (ESI, m/z): Calcd. for C18H19N3O2, 310.1 (M+H), found 310.2. as prepared in the previous step)

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

実験手順: Using a procedure similar to Example 3, step (c), 1-(2-methyl-6-nitro-phenyl)-piperidine (74 mg, 0.38 mmol, as prepared in the previous step) was stirred with 5% Pd—C (50 mg) under H2 to afford 66 mg (91%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C12H18N2, 191.1 (M+H), found 191.1. as prepared in the previous step)

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

実験手順: Using a procedure similar to example 3, step (d), 3-methyl-2-piperidin-1-yl-phenylamine (68 mg, 0.35 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (65 mg, 0.42 mmol) in the presence of DIEA (134 μL, 0.77 mmol) to afford 13 mg (12%) of the title compound as a waxy yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 10.7 (br s, 1H), 8.33 (d, 1H, J=8.0 Hz), 7.27 (d, 1H, J=3.7 Hz), 7.22 (dd, 1H, 3.7 Hz), 7.12 (t, 1H, J=7.9 Hz), 6.87 (dd, 1H, J=0.7, 7.7 Hz), 3.22-3.28 (m, 2H), 2.88-2.91 (m, 1H), 2.41 (s, 3H), 2.01-2.04 (m, 1H), 1.80-1.86 (m, 4H), 1.43-1.47 (m, 1H); Mass spectrum (ESI, m/z): Calcd. for C18H19N3O2, 310.1 (M+H), found 310.2. as prepared in the previous step)

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

実験手順: Using a procedure similar to Example 3, step (c), 1-(2-methyl-6-nitro-phenyl)-piperidine (74 mg, 0.38 mmol, as prepared in the previous step) was stirred with 5% Pd—C (50 mg) under H2 to afford 66 mg (91%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C12H18N2, 191.1 (M+H), found 191.1. as prepared in the previous step)

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

実験手順: Using a procedure similar to example 3, step (d), 3-methyl-2-piperidin-1-yl-phenylamine (68 mg, 0.35 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (65 mg, 0.42 mmol) in the presence of DIEA (134 μL, 0.77 mmol) to afford 13 mg (12%) of the title compound as a waxy yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 10.7 (br s, 1H), 8.33 (d, 1H, J=8.0 Hz), 7.27 (d, 1H, J=3.7 Hz), 7.22 (dd, 1H, 3.7 Hz), 7.12 (t, 1H, J=7.9 Hz), 6.87 (dd, 1H, J=0.7, 7.7 Hz), 3.22-3.28 (m, 2H), 2.88-2.91 (m, 1H), 2.41 (s, 3H), 2.01-2.04 (m, 1H), 1.80-1.86 (m, 4H), 1.43-1.47 (m, 1H); Mass spectrum (ESI, m/z): Calcd. for C18H19N3O2, 310.1 (M+H), found 310.2. as prepared in the previous step)

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

実験手順: Using a procedure similar to Example 3, step (c), 1-(2-methyl-6-nitro-phenyl)-piperidine (74 mg, 0.38 mmol, as prepared in the previous step) was stirred with 5% Pd—C (50 mg) under H2 to afford 66 mg (91%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C12H18N2, 191.1 (M+H), found 191.1. as prepared in the previous step)