Dimethylformamide → HCID 69223440, compound

Participants

Reaction Steps

A solution of benzoximidazole (10.4 mg) in anhydrous DMF (1.5 mL) under argon was cooled to 0-5° C. Sodium bis(trimethylsilyl)amide (0.6 M in toluene, 129 μL) was added via micropipette followed by 2-[2,4-dioxo-3-(methanesulfonyloxymethylene)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide [containing approximately 40% of 2-[2,4-dioxo-3-methylene-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide](12s, 20mg). The reaction was allowed to warm to ambient temperature and stir overnight. Addition sodium bis(trimethylsilyl)amide (0.6 M in toluene, 129 μL) was added via micropipette. After approximately 10 min., the reaction mixture was quenched with several drops of glacial acetic acid and evaporated in vacuo. The residue was partitioned between ethyl acetate and aqueous 1N NaHSO4. The layers were separated and the aqueous layer was back-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified on a preparative TLC plate (20×20 cm, 500 μM) eluting with 5% methanol in CH2Cl2. The product band was removed, eluted with 4:1 CH2Cl2/methanol, filtered and evaporated in vacuo. The residue was lyophilized from CH3CN/H2O to provide 2-[2,4-dioxo-3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)methylene-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (10 mg) as a white lyophilate. 1H NMR (400 MHz, CDCI3) 0.99 (m, 6H), 3.62 (d, J=16 Hz, 1H), 3.79 (s, 3H), 4.10 (d, J=16 Hz, 1H), 4.23 (t, J=6 Hz, 1H), 4.50 (m, 2H), 4.90 (m, 1H), 5.86 (d, J=6 Hz, 1H), 5.91 (d, J=6 Hz, 1H), 6.99 (m, 7H), 7.26 (m, 3H), 7.33 (m, 2H), 7.46 (d, J=8 Hz, 1H), 7.54 (s, 1H).

Provenance & Evidence