Acetic Acid → HCID 11487616, compound

Participants

Reaction Steps

A stirred mixture of 2-amino-5-iodobenzoic acid (1.0 g), trimethyl orthoformate (0.83 ml), and acetic acid (0.022 ml) in toluene (15 ml) was heated under reflux for 2 hours. 3-Amino-N-cyclopropyl-4-methylbenzamide (0.65 g) was added to the reaction mixture and stirred at reflux for 16 hours. The reaction mixture was allowed to cool and diluted with ethyl acetate. The organic solution was then washed with 1N HCl solution, 2N NaOH solution (x 2), brine, dried (magnesium sulfate), and concentrated to give N-cyclopropyl-3-(6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide (AZ12233711) (1.22 g) as an off white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 2.14 (s, 3H), 2.85 (m, 1H), 7.52 (d, 1H), 7.58 (d, 1H), 7.88 (s, 1H), 7.92 (d, 1H), 8.20 (d, 1H), 8.34 (s, 1H), 8.42 (d, 1H), 8.49 (s, 1H); Mass Spectrum: M+H+ 446.

Provenance & Evidence