Water → HCID 59536274, compound

Participants

Reaction Steps

To a solution of 5-amino-2-pyridinecarbonitrile (81 mg, 678 μmol) in THF (1.0 mL) was added sodium hydride, 60% dispersion in mineral oil (17 mg, 452 μmol). The resulting mixture was then subjected to a microwave irradiation at 160° C. for 15 min. Then, (R)-4-nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (100 mg, 226 example 88) was added and the mixture was stirred at RT for overnight. Then, H2O (0.5 mL) was added and the mixture was extracted with EtOAc (2×1 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was dissolved in DMSO (1.0 mL) and the solution was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired compound, which was dissolved in MeOH (1.0 mL). The solution was then washed through PL-HCO3 MP-Resin (200 mg per 6 mL tube) and the resin was washed with MeOH (2×0.3 mL). The combined washings were concentrated and dried under vacuum to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 423 (M+H).

Provenance & Evidence