C([O:3][C:4]([C:6]1([C:15](=[O:27])[NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][N:21]=[CH:22]3)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO.O>CO.C(Cl)Cl>[CH:22]1[C:23]2[C:18](=[C:17]([NH:16][C:15]([C:6]3([C:4]([OH:5])=[O:3])[CH2:7][C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:14]3)=[O:27])[CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][N:21]=1A 30 mL reaction vial is charged with 2-(isoquinolin-5-ylcarbamoyl)-indan-2-carboxylic acid ethyl ester (320, 354 mg, 0.98 mmol) is charged with 1,4-dioxane (6 mL) and MeOH (6 mL). A stirring bar is added and stirring is initiated. After dissolution, water (3 mL) is added followed by the LiOH monohydrate (104 mg, 252 mmol). After 20 h, tlc analysis (silica, 10% MeOH/DCM) indicates that the starting material is completely consumed. Amberlyst highly acidic exchange resin (1 g) is added to the reaction vial. The reaction is capped and allowed to stir at ambient temperature. After 64 h, the contents of the flask are filtered through a pad of Celite. The solvent is removed from the filtrate by pumping to constant weight to give 0.29 g of off white solid. This material is triturated with DCM (15 mL). The solids are collected by suction filtration and washed with DCM (20 mL). Suction drying provides off white solid (280 mg, 86%).
불러오는 중…
