Hydrazine hydrate (1:1) → HCID 86727586, compound

Participants

Reaction Steps

To a mixture of (R)-2-(7-bromo-3-thioxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propionic acid ethyl ester (60 g, 174 mmol) in EtOH (800 mL) was added hydrazine hydrate (98%, 17.4 g, 349 mmol) and the reaction mixture was stirred at ambient temperature overnight. The precipitate was collected by filtration and washed with cold EtOH (3×80 mL) to give (R)-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (32.5 g, 59%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.82 (s, 1H), 7.23 (s, 1H), 7.21 (s, 2H), 4.78 (q, J=6.8 Hz, 1H), 4.68-4.60 (m, 2H), 1.29 (d, J=6.8 Hz, 3H). SFC (Table 1, Method 31) Rt=6.114 min.; [α]D20=−342.08 (C=0.002 g/mL in methanol).

Provenance & Evidence