Diisopropylcarbodiimide → 3-(benzo[d][1,3]dioxol-5-yl)-N-(1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)propanamide

Participants

Reaction Steps

Typical procedure: To a suspension of PS-DIC 110 mg/well (Argonaut, 1.38 mmol/g loading) in DCE (0.5 mL) at room temperature was added HOBt (5 mg in 100 μL DMF), followed by 3-(benzo[d][1,3]dioxol-5-yl)propanoic acid (75 μmol). To this was added 1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-amine, dihydrochloride (14 mg, 50 μmol), prepared as described in Example 19C, in 1,2-dichloroethane (0.5 mL). The reaction mixture was shaken at RT for 24 h, contents were filtered into a synthesis tube rack (STR) and the solvent was dried in a speed vac. The resulting residue was chromatographed using preparative HPLC (conditions: Xterra MS-C18 (30×50 mm); eluted with 10% to 100% B, 6 min gradient. (A=100% water with 0.1% TFA and B=acetonitrile with 0.1% TFA); flow rate at 30 mL/min; UV detection at 220 nm) to give the title compound, 3-(benzo[d][1,3]dioxol-5-yl)-N-(1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)propanamide, (2.2 mg, 8%). HPLC (method C): retention time=1.6 min, MS (ES): m/z 449 [M+H]+.

Provenance & Evidence