Benzenesulfonic Acid → Crenolanib Besylate
반응식
[CH3:1][C:2]1([CH2:6][O:7][C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:15]4[CH:24]=[CH:23][C:22]5[C:17](=[C:18]([N:25]6[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]6)[CH:19]=[CH:20][CH:21]=5)[N:16]=4)[CH:13]=[N:14][C:10]=3[CH:9]=2)[CH2:5][O:4][CH2:3]1.[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C>[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH3:1][C:2]1([CH2:6][O:7][C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:15]4[CH:24]=[CH:23][C:22]5[C:17](=[C:18]([N:25]6[CH2:26][CH2:27][CH:28]([NH2:31])[CH2:29][CH2:30]6)[CH:19]=[CH:20][CH:21]=5)[N:16]=4)[CH:13]=[N:14][C:10]=3[CH:9]=2)[CH2:5][O:4][CH2:3]1참가 물질
4
실험 절차
The compound, 1-{2-[5-(3-Methyl-oxetan-3-ylmethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine (2.44 9, 5.5 mmol, 1 equivalent) and ethanol (24 mL, 10 volumes) were added to a 100 mL round bottom flask. The solution was heated to reflux to dissolve the starting material and then cooled to room temperature. A solution of benzenesulfonic acid (918 mg, 5.2 mmol, 0.95 equivalents) in ethanol (5 mL, 2 volumes) was charged and the reaction was heated to reflux for ˜30 minutes. The reaction was cooled to 20–30° C. and allowed to granulate for 16–32 hours. The material was then filtered and dried under vacuum with a slight nitrogen bleed to afford 1-{2-[5-(3-Methyl-oxetan-3-ylmethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine benzenesulfonate (2.8 g, 85% yield) as an off-white solid.