1,4-Dioxane hydrochloride → C-[4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-yl]-methylamine
Reaktionsgleichung
C(OC(=O)[NH:7][CH2:8][CH:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]=3[N:18]=[CH:17][N:16]=2)[CH2:10]1)(C)(C)C.Cl.O1CCOCC1>CO>[N:18]1[C:19]2[NH:20][C:21]3[C:26]([C:27]=2[C:15]([N:11]2[CH2:12][CH2:13][O:14][CH:9]([CH2:8][NH2:7])[CH2:10]2)=[N:16][CH:17]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of [4-(9H-pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester (0.021 g, 0.548 mmol) and 4M HCl-dioxane (1 mL) in methanol (5 mL) was stirred at room temperature for 2.5 hours. The solution was evaporated to dryness and purified by Ion exchange on SCX-II acidic resin (2 g) eluting with methanol, then 2 M ammonia-methanol. The basic fractions were combined. Preparative silica TLC, eluting with 1% ammonia—9% methanol—90% dichloromethane, gave the title compound (0.007 g, 0.025 mmol, 46%) as a beige powder. 1H NMR (500 MHz, CD3OD) δ 2.75-2.80 (2H, m), 3.00-3.06 (1H, m), 3.35-3.40 (1H, m), 3.75-3.85 (1H, m), 3.90 (1H, dd, J=10.10 Hz), 4.10-4.13 (1H, m), 4.19 (1H, d, J=13 Hz), 4.25 (1H, d, J=13 Hz), 7.35 (1H, dd, J=8.8 Hz), 7.47 (1H, dd, J=8.8 Hz), 7.57 (1H, d, J=8 Hz), 7.79 (1H, d, J=8 Hz), 8.46 (1H, s); LC-MS (3) Rt 1.98 min; m/z (ESI) 284 [MH+].