1,1'-Carbonyldiimidazole → HCID 136038645, compound

Participants

Reaction Conditions

Reaction Steps

A solution C-(3-benzyloxy-phenyl)-C-(3-chloro-pyrazin-2-yl)-methylamine hydrochloride (5 g, 13.8 mmol) and CDI (2.46 g, 15.19 mmol) in anhydrous THF (70 mL) was charged with DIEA (2.40 mL, 13.8 mmol) and heated to 80° C. for 1 h and then concentrated in vacuo. The crude material was partitioned between EtOAc and H2O and separated. The aqueous layer was washed with EtOAc (3×) and the combined organic layers were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by chromatography on silica gel [eluting with 5% MeOH in DCM], to yield the desired product as a yellow solid; 1H NMR (DMSO-d6, 400 MHz) δ 5.17 (s, 2H), 6.86 (d, J=5.2 Hz, 1H), 7.10-7.16 (m, 2H), 7.22-7.23 (m, 1H), 7.34-7.48 (m, 6H), 7.50 (d, J=7.9 Hz, 1H); MS (ES+): m/z=352.15 (100) [MH+], HPLC: tR=3.19 min (MicromassZQ, polar—5 min)

Provenance & Evidence