Aziridine → HCID 11279428, compound

Participants

Reaction Steps

A stirred suspension of the above benzamide (150 mg, 0.44 mmol) in THF (40 mL) was treated with aziridine (91 μL, 1.76 mmol) at room temperature for 4 h, then additional aziridine (91 μL) was added. After a further 4 h, the mixture was concentrated under reduced pressure below 25° C., and the residue was partitioned between EtOAc and saturated NaCl. Evaporation of the organic layer gave a product that was triturated with EtOAc then recrystallized from MeCN/EtOAc/petroleum ether to give 7 (56 mg, 37%): mp >250° C.; 1H NMR [(CD3)2SO] δ8.91 (t, J=5.6 Hz, 1H, NH), 8.66 (s, 1H, H-3), 7.67 (s, 1H, imidazole-H), 7.29 (s, 1H, H-6), 7.24 & 6.93 (2xs, 2H, imidazole-H), 4 16 (t, J=5.9 Hz, 2H, NHCH2CH2), 3 62-3.51 (m, 2H, NHCH2), 2.49 (s, 4H, aziridine-H). Anal. Calcd. for C14H14N6O5: C, 48.55;H, 4.07; N, 24.27. Found: C, 48.69;H, 4.00; N, 24.10%.

Provenance & Evidence