O-methylhydroxylammonium chloride → tert-Butyl (1-(4-(2-(methoxyimino)-1-methyl-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

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Reaction Steps

In a round-bottomed flask was added tert-butyl 1-(4-(1-methyl-7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (0.1 g, 0.199 mmol) and o-methylhydroxylamine hydrochloride (0.067 g, 0.797 mmol) in Pyridine (Volume: 2 ml). The resulting solution was stirring and heating at 70 degree for 18 h. The reaction mixture was concentrated to dryness and partitioned between ethyl acetate (20 ml) and water (20 ml). The organic phase was separated and washed with water (2×15 ml), brine (15 ml) concentrated to give the crude product which was purified by column (biotage, 25 g) eluted with ethyl acetate/cyclohexane (0-50%) to give product (21 mg) 1H NMR (500 MHz, CDCl3) 7.20-7.29 (m, 9H), 7.10 (s, 1H), 5.19 (s, 2H), 4.95 (s, 1H), 3.81 (s, 3H), 3.31 (s, 3H), 2.2-2.6 (m, 4H), 1.95-2.15 (m, 1H), 1.75-1.85 (m, 1H), 1.2-1.4 (br, 9H).

Provenance & Evidence