Trifluoroacetic acid → HCID 69075034, compound

Participants

Reaction Steps

To a solution of 5-[4-(4-chloropyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 40 (0.220 g, 0.459 mmol) in anhydrous dichloromethane (10 mL) was added trifluoroacetic acid (4.190 g, 36.744 mmol) at 0° C., the reaction mixture was warmed to room temperature and stirred at the same temperature for 2 h. The mixture was concentrated under reduced pressure, repeatedly evaporated using dichloromethane. The residue was treated with aqueous HCl and filtered. The filtrates were basified using 1N NaOH, extracted with CHCl3, washed with water, dried over Na2SO4 and evaporated under reduced pressure. The oily mass was dissolved in MeOH (15 mL) and then in diethyl ether (60 mL). 2 M HCl solution in diethylether (30 mL) was added to above solution at 0° C., the mixture was warmed to room temperature and stirred overnight. Filtered the reaction mixture, the residue was washed with ether, crystallized from methanol-ether to afford 42 as off white-solid (0.103 g, 50%). 1H NMR (300 MHz, DMSO-d6) δ 9.33 (bs, 2H, —NH2), 8.62 (s, 1H, ArH), 8.59 (d, J=5.4 Hz, 1H, ArH), 7.76 (d, J=5.4 Hz, 1H, ArH), 7.55 (s, 4H, ArH), 6.83 (s, 1H, ArH), 6.79 (s, 1H, ArH), 6.00 (s, 2H, —CH2), 4.72 (s, 1H, —CH—), 3.48-3.17 (m, 4H, 2*—CH2), 3.08-2.86 (m, 2H, —CH2). MS (ES+) m/z 379 [M-(2HCl)+H]+.

Provenance & Evidence