Acetonitrile → n-[6-Chloro-2-[methyl[3-(methylamino)propyl]amino]-5-quinolinyl]-1-cyclohexyl-cyclopropanecarboxamide, hydrochloride
反応式
[CH:1]1([C:7]2([C:10]([NH:12][C:13]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][C:17](Cl)=[N:18]4)=[O:11])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH2:30].[C:32](#N)C>>[ClH:23].[Cl:23][C:22]1[C:13]([NH:12][C:10]([C:7]2([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH2:9][CH2:8]2)=[O:11])=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([N:30]([CH3:32])[CH2:29][CH2:28][CH2:27][NH:26][CH3:31])[CH:16]=[CH:15]2参加物
4
反応条件
- 温度
- 100 °C
実験手順
To a 10 mL vial was added 1-cyclohexyl-N-(2,6-dichloro-5-quinolinyl)-cyclopropanecarboxamide (example 26 (b)) (0.13 g), N,N-dimethyl-1,3-propanediamine (0.13 mL) and acetonitrile (3 mL). The vial was sealed and heated at 100° C. in a microwave for 20 minutes followed by 30 minutes at 110° C. The solvent was removed from the cooled reaction under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (30 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organics were washed with water (50 mL) and brine (50 mL) before being dried, filtered and concentrated. Purification (Varian SCX cartridge, using methanol and 10% ammonia in methanol as eluant) gave a crude product which was further purified by chromatography (SiO2, ammonia:methanol:dichloromethane, 1:2.5:96.5 as eluant). The product was converted to its hydrochloride salt by dissolution in dichloromethane and treatment with 4M hydrogen chloride in 1,4 dioxane (5 mL). Removal of volatiles and recrystallisation from methanol/acetonitrile afforded the title compound (0.075 g).