Dimethylformamide → HCID 59297029, compound

Participants

Reaction Steps

To a stirred solution of [1-benzyl-6-(2H-tetrazol-5-yl)-1,2,3,4-tetrahydroquinolin-3-yl]-carbamic acid cyclohexyl ester (61 mg, 0.14 mmol), prepared as described in Example 53, in CH3CN (0.5 mL)-DMF (0.5 mL)-THF (0.5 mL) at RT was added Cs2CO3 (63.4 mg, 0.19 mmol), followed by iodomethane (7.8 μL, 0.126 mmol). The reaction mixture was stirred at RT for 16 h and then diluted with H2O, extracted with EtOAc (10 mL×3). The organic extracts were washed saturated aqueous NaCl, dried Na2SO4), and concentrated. The resulting residue was purified using preparative HPLC [YMC S5 ODS (20×100 mm); Eluted with 50% to 90% B, 8 min gradient and 7 min hold. (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH); Flow rate at 20 mL/min. UV detection at 220 nm] to give the title compound (regioisomer A, 35 mg, 56%) as a white solid. HPLC (method B): 98% pure, retention time=7.9 min. MS (ES): m/z 447 [M+H]+.

Provenance & Evidence