Morpholine → HCID 11395588, compound

Participants

Reaction Steps

Morpholine (0.21 ml) was added to a stirred solution of N-(5-[(cyclopropylamino)carbonyl]-2-methylphenyl)-5-fluoro-2-nitrobenzamide (0.71 g) in DMSO (1.0 ml). The mixture was stirred at room temperature for 18 hours. The mixture was poured into a saturated NaHCO3 solution (100 ml) and the resultant solid was filtered and dried under vacuum at 40° C. There was thus obtained N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholin-4-yl-2-nitrobenzamide (0.722 g); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.68 (m, 2H), 2.29 (s, 3H), 2.83 (m, 1H), 3.45 (m, 4H), 3.74 (m, 4H), 7.07 (m, 2H), 7.28 (m, 1H), 7.56 (m, 1H), 7.95 (s, 1H), 8.06 (d, 1H), 8.36 (s, 1H), 9.92 (s, 1H); Mass Spectrum: M+Na+ 447. B) 10% Palladium-on-carbon (0.050 g) was added to a stirred suspension of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholinyl-2-nitrobenzamide (0.722 g) in ethanol (10 ml) and the mixture was stirred under an atmosphere of hydrogen gas at a pressure of 10 bar. After cessation of hydrogen uptake, the catalyst was removed by filtration through diatomaceous earth (Celite®). The filtrate was concentrated under reduced pressure, which provided the crude 2-amino-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholin-4-ylbenzamide which was used without further purification; Mass Spectrum: M+H+ 395.

Provenance & Evidence