HCID 58902037, compound → HCID 58901999, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-[(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-oxalamic acid ethyl ester (50 mg, 0.12 mmol) in POCl3 (2 mL) was heated to 55° C. for 17.5 h. Very little reaction occurred therefore DMF (3 drops) was added to reaction mixture and heated to 75° C. overnight. The brown reaction mixture was allowed to cool to rt, concentrated in vacuo and then quenched with 2M NH3 in i-PrOH at 0° C. until the pH was basic. The reaction mixture was concentrated in vacuo and the crude material was purified by chromatography on silica gel [eluting with 2% EtOAc in DCM], resulting in the title compound as an off-white solid; 1H NMR (CDCl3, 400 MHz) δ 1.48 (t, J=7.2 Hz, 3H), 4.56 (q, J=7.2 Hz, 2H), 5.13 (s, 2H), 7.05-7.09 (m, 1H), 7.22-7.29 (m, 2H), 7.29-7.47 (m, 6H), 7.67 (d, J=5.2 Hz, 1H), 9.15 (d, J=5.2 Hz, 1H); MS (ES+): m/z=408.07 (100) [MH+], HPLC: tR=3.88 min (MicromassZQ, polar—5 min).

Provenance & Evidence