Diethyl Malonate → HCID 68637520, compound

Participants

Reaction Conditions

Reaction Steps

3-Nitro-benzene-1,2-diamine (5.0 g) was dissolved in diethyl malonate. The reaction was heated at 160° C. oil bath for 48 h. After cooling to rt, flash chromatography of the crude reaction gave (4-nitro-1H-benzoimidazol-2-yl)-acetic acid (4.50 g). MS found: (M+H)+=250.0 (2b) A portion (500 mg) of the above derivative (20a) was dissolved in THF (6 ml) prior to the addition of a solution of LiOH.H2O (100 mg) in water (0.3 ml). A couple drops of MeOH were added until the solution became clear. After 3 h at rt, the reaction was concentrated and freeze-dried to provide (4-nitro-1H-benzoimidazol-2-yl)-acetic acid lithium salt (482 mg). 1H NMR (DMSO, δ ppm, 300 mHz) 3.57 (s, 2H), 7.15 (t, 1H), 7.81 (d, 1H), 7.9 (d, 1H). (2c) Derivative (2b) (50 mg) was incorporated into example (1e) to give the title compound (63 mg). MS found: (M+H)+=468.3.

Provenance & Evidence