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1
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 92%).
m.p.: 220-222 C. HPLC: 96.0%. H NMR (400 MHz, CDCl3) δ
7.46 (dd, J = 7.2, 2.0 Hz, 1H), 7.28 (dd, J = 7.2, 2.0 Hz, 1H),
7.17-7.10 (m, 2H), 5.66 (s, 1H), 4.36-4.28 (m, 1H), 4.15 (s, 1H),
3.37-3.33 (m, 1H), 3.27-3.20 (m, 1H), 3.07-2.98 (m, 1H), 2.63-
2.61 (m, 2H), 2.52-2.47 (m, 1H), 1.97-1.80 (m, 2H), 1.76-1.65
(m, 1H), 1.52-1.48 (m, 1H), 1.41-1.36 (m, 1H), 1.27 (d, J = 6.4
Hz, 3H), 1.25 (d, J = 6.4 Hz, 3H), 1.00 (t, J = 7.2 Hz, 3H), 0.96-
1.03 (m, 4H); ESI-MS (m/z): 364 [M+H]+. HRMS (ESI): m/z
[M+H]+ calcd for C23H30N3O: 364.2389, Found: 364.2386.
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1
m.p.: 210-212 C. HPLC: 96.1%. H NMR (400 MHz, CDCl3) δ
7.46 (dd, J = 7.2, 2.0 Hz, 1H), 7.26 (dd, J = 7.2, 2.0 Hz, 1H),
7.17-7.10 (m, 2H), 5.95 (s, 1H), 5.68 (s, 1H), 4.15 (s, 1H), 3.50-
3.48 (m, 2H), 3.38-3.33 (m, 1H), 3.28-3.20 (m, 1H), 3.07-2.98
(m, 1H), 2.63-2.61 (m, 2H), 2.52-2.47 (m, 1H), 1.95-1.82 (m,
2H), 1.74-1.70 (m, 1H), 1.52-1.48 (m, 1H), 1.42-1.37 (m, 1H),
1.28-1.26 (t, J = 7.2 Hz, 3H), 1.04-0.96 (m, 4H); 13C NMR (101
MHz, CDCl3) δ 164.0, 133.7, 131.9, 131.3, 129.3, 122.1, 121.9,
120.4, 118.5, 112.0, 108.9, 56.0, 51.6, 45.1, 37.4, 35.0, 29.4, 27.5,
20.5, 16.5, 14.8, 8.8; ESI-MS (m/z): 350 [M+H]+. HRMS (ESI):
m/z [M+H]+ calcd for C22H28N3O: 350.2232, Found: 350.2227.
3.2.14. (41S,13aS)-N-cyclopentyl-13a-ethyl-2,3,41,5,6,13a-
hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]-
naphthyridine-12-carboxamide (Vin-B08)
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 81%).
3.2.10. (41S,13aS)-13a-ethyl-N-propyl-2,3,41,5,6,13a-hexahydro-
1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-
carboxamide (Vin-B04)
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m.p.: 152-154 C. HPLC: 96.1%. H NMR (400 MHz, CDCl3) δ
7.46 (dd, J = 7.2, 2.0 Hz, 1H), 7.27 (dd, J = 7.2, 2.0 Hz, 1H),
7.17-7.10 (m, 2H), 5.87-5.85 (m, 1H), 5.68 (s, 1H), 4.49-4.40 (m,
1H), 4.15 (s, 1H), 3.38-3.33 (m, 1H), 3.28-3.20 (m, 1H), 3.07-
2.98 (m, 1H), 2.63-2.60 (m, 2H), 2.52-2.47 (m, 1H), 2.15-2.09
(m, 2H), 1.94-1.80 (m, 3H), 1.72-1.65 (m, 5H), 1.52-1.46 (m,
2H), 1.44-1.37 (m, 1H), 1.02-0.96 (m, 4H); 13C NMR (101 MHz,
CDCl3) δ 163.6, 133.6, 131.8, 131.4, 129.2, 122.0, 121.9, 120.4,
118.4, 112.1, 108.9, 56.0, 51.7, 51.6, 45.1, 37.4, 33.2, 32.8, 29.3,
27.5, 23.9, 23.8, 20.5, 16.5, 8.8; ESI-MS (m/z): 390 [M+H]+.
HRMS (ESI): m/z [M+H]+ calcd for C25H32N3O: 390.2545,
Found: 390.2541.
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 89%).
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m.p.: 266-268 C. HPLC: 96.7%. H NMR (400 MHz, CDCl3) δ
7.46 (d, J = 7.2 Hz, 1H), 7.27-7.25 (m, 1H), 7.17-7.10 (m, 2H),
5.99-5.96 (t, J = 5.6 Hz, 1H), 5.67 (s, 1H), 4.16 (s, 1H), 3.50-3.33
(m, 3H), 3.28-3.21 (m, 1H), 3.07-2.98 (m, 1H), 2.64-2.61 (m,
2H), 2.53-2.47 (m, 1H), 1.94-1.82 (m, 2H), 1.78-1.73 (m, 1H),
1.68-1.62 (m, 2H), 1.52-1.49 (m, 1H), 1.42-1.37 (m, 1H), 1.05-
0.97 (m, 7H); 13C NMR (101 MHz, CDCl3) δ 164.1, 133.7, 131.9,
131.1, 129.2, 122.1, 121.7, 120.4, 118.5, 112.0, 108.9, 56.0, 51.6,
45.1, 41.8, 37.4, 29.4, 27.5, 22.8, 20.5, 16.4, 11.6, 8.8; ESI-MS
(m/z): 364 [M+H]+. HRMS (ESI): m/z [M+H]+ calcd for
C23H30N3O: 364.2389, Found: 364.2384.
3.2.15. (41S,13aS)-13a-ethyl-N-(2-hydroxyethyl)-2,3,41,5,6,13a-
hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]-
naphthyridine-12-carboxamide (Vin-B09)
3.2.11. (41S,13aS)-N-butyl-13a-ethyl-2,3,41,5,6,13a-hexahydro-
1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-
carboxamide (Vin-B05)
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 79%).
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m.p.: 191-193 C. HPLC: 97.0%. H NMR (400 MHz, CDCl3) δ
7.45 (d, J = 6.4 Hz, 1H), 7.24 (d, J = 6.4 Hz, 1H), 7.16-7.08 (m,
2H), 6.54-6.52 (m, 1H), 5.69 (s, 1H), 4.11 (s, 1H), 3.77 (t, J = 5.6
Hz, 2H), 3.67- 3.59 (m, 1H), 3.56-3.49 (m, 1H), 3.43 (s, 1H),
3.33- 3.28 (m, 1H), 3.20-3.13 (m, 1H), 3.04-2.95 (m, 1H), 2.61-
2.57 (m, 2H), 2.50-2.44 (m, 1H), 1.94-1.78 (m, 2H), 1.74-1.62
(m, 1H), 1.51-1.43 (m, 1H), 1.42-1.34 (m, 1H), 1.02-0.94 (m,
4H); 13C NMR (101 MHz, CDCl3) δ 165.0, 133.7, 131.6, 130.9,
129.2, 122.2 (2C), 120.5, 118.5, 111.9, 108.9, 61.7, 55.9, 51.5,
45.0, 42.6, 37.4, 29.2, 27.4, 20.4, 16.4, 8.8; ESI-MS (m/z): 366
[M+H]+. HRMS (ESI): m/z [M+H]+ calcd for C22H28N3O2:
366.2182, Found: 366.2177.
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 86%).
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m.p.: 259-261 C. HPLC: 93.5%. H NMR (400 MHz, CDCl3) δ
7.43 (dd, J = 7.2, 2.0 Hz, 1H), 7.22 (dd, J = 7.2, 2.0 Hz, 1H),
7.13-7.06 (m, 2H), 6.31-6.24 (m, 1H), 5.60 (s, 1H), 4.11 (s, 1H),
3.43-3.28 (m, 3H), 3.23-3.15 (m, 1H), 3.04-2.95 (m, 1H), 2.60-
2.56 (m, 2H), 2.48-2.43 (m, 1H), 1.93-1.75 (m, 2H), 1.72-1.61
(m, 1H), 1.58-1.51 (m, 2H), 1.45-1.42 (m, 1H), 1.38-1.30 (m,
3H), 1.09-0.91 (m, 7H); 13C NMR (101 MHz, CDCl3) δ 164.1,
133.6, 131.8, 131.0, 129.1, 121.9, 121.2, 120.2, 118.3, 111.9,
108.6, 55.8, 51.5, 45.0, 39.7, 37.1, 31.4, 29.4, 27.3, 20.4, 20.1,
16.3, 13.7, 8.7; ESI-MS (m/z): 378 [M+H]+. HRMS (ESI): m/z
[M+H]+ calcd for C24H32N3O: 378.2545, Found: 378.2542.
3.2.16. (41S,13aS)-13a-ethyl-N-(3-hydroxypropyl)-2,3,41,5,6,13a-
hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-
ij][1,5]naphthyridine-12-carboxamide (Vin-B10)
3.2.12. (41S,13aS)-13a-ethyl-N-pentyl-2,3,41,5,6,13a-hexahydro-
1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-
carboxamide (Vin-B06)
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 75%).
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1
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 88%).
m.p.: 203-205 C. HPLC: 95.1%. H NMR (400 MHz, CDCl3) δ
7.46 (d, J = 6.4 Hz, 1H), 7.24 (d, J = 6.4 Hz, 1H), 7.17-7.10 (m,
2H), 6.52-6.49 (m, 1H), 5.72 (s, 1H), 4.13 (s, 1H), 3.73 (t, J = 5.6
Hz, 2H), 3.69-3.54 (m, 2H), 3.36-3.31 (m, 1H), 3.25-3.18 (m,
1H), 3.06-2.97 (m, 1H), 2.62-2.56 (m, 2H), 2.53-2.46 (m, 1H),
1.96-1.85 (m, 2H), 1.83-1.78 (m, 2H), 1.75-1.64 (m, 1H), 1.53-
1.44 (m, 1H), 1.42-1.34 (m, 1H), 1.03-0.95 (m, 4H); ESI-MS
(m/z): 380 [M+H]+. HRMS (ESI): m/z [M+H]+ calcd for
C23H30N3O2: 380.2338, Found: 380.2336.
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1
m.p.: 227-230 C. HPLC: 90.8%. H NMR (400 MHz, CDCl3) δ
7.47 (dd, J = 6.4, 2.0 Hz, 1H), 7.25 (dd, J = 6.4, 2.0 Hz, 1H),
7.17-7.10 (m, 2H), 5.96 (m, 1H), 5.67 (s, 1H), 4.15 (s, 1H), 3.54-
3.40 (m, 2H), 3.38-3.33 (m, 1H), 3.28-3.20 (m, 1H), 3.07-2.98
(m, 1H), 2.63-2.61 (m, 2H), 2.52-2.47 (m, 1H), 1.97-1.83 (m,
2H), 1.82-1.80 (m, 1H), 1.77-1.67 (m, 1H), 1.65-1.58 (m, 2H),
1.52-1.48 (m, 1H), 1.37-1.34 (m, 4H), 1.05-0.98 (m, 4H), 0.92 (t,
J = 7.2 Hz, 3H); ESI-MS (m/z): 392 [M+H]+. HRMS (ESI): m/z
[M+H]+ calcd for C25H34N3O: 392.2702, Found: 392.2698.
3.2.17. (41S,13aS)-13a-ethyl-N-phenyl-2,3,41,5,6,13a-hexahydro-
1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-
carboxamide (Vin-B11)
3.2.13. (41S,13aS)-13a-ethyl-N-isopropyl-2,3,41,5,6,13a-
hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]-
naphthyridine-12-carboxamide (Vin-B07)
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 72%).
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1
The crude product was purified by flash chromatography
(DCM/MeOH = 50/1) to give a light yellow solid (Yield 85%).
m.p.: 176-178 C. HPLC: 97.1%. H NMR (400 MHz, CDCl3) δ
8.08 (s, 1H), 7.56 (d, J = 8.0 Hz, 2H), 7.49-7.46 (m, 1H), 7.30 (d,