Sodium hydride → HCID 66919042, compound

Participants

Reaction Steps

To a solution of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-fluoro-2-nitrobenzamide (2.0 g) and tert-butyl 4-hydroxy-1-piperidinecarboxylate (1.69 g) in DMF (30 ml) was added sodium hydride (0.896 g of a 60% dispersion in oil) portion-wise (ice bath cooling). The reaction was stirred for 22 hours at room temperature under an atmosphere of argon. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution (200 ml) and the resulting precipitate was collected by filtration, washed with diethyl ether, and air dried to yield tert-butyl 4-{3-[({5-[(cyclopropylamino)carbonyl]-2-methylphenyl}amino)carbonyl]-4-nitrophenoxy}piperidine-1-carboxylate (2.76 g) as a yellow solid; NMR Spectrum: (DMSOd6) 0.60 (m, 2H), 0.70 (m, 2H), 1.40 (s, 9H), 1.60 (m, 2H), 1.97 (m, 2H), 2.30 (s, 3H), 2.84 (m, 1H), 3.23 (m, 2H), 3.66 (m, 2H), 4.88 (m, 1H), 7.29 (m, 2H), 7.31 (s, 1H), 7.60 (d, 1H), 7.95 (s, 1H), 8.17 (d, 1H), 8.38 (d, 1H), 10.10 (s, 1H); Mass Spectrum: M+Na+ 561.

Provenance & Evidence