Hydrazine → 4-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(morpholin-4-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzohydrazide

Participants

Reaction Steps

Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(morpholin-4-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzoate (EXAMPLE 34 Step A, 0.051 g, 0.067 mmol) was dissolved in ethanol (0.45 mL). Added hydrazine (0.063 mL, 2.014 mmol) and stirred at 85° C. in a screw cap vial (pressure relief type) under a nitrogen blanket. Once complete, the solvent was removed by rotary evaporation and the crude isolate was partitioned between ethyl acetate and water. Washed the organic twice more with water, then once with brine, dried over sodium sulfate, filtered and evaporated to give an off-white foam as the product. The compound was used without further purification. 1H NMR (CDCl3, 500 MHz): δ 8.16 (s, 1H), 8.00 (d, 1H), 7.88 (s, 1H), 7.73 (s, 2H), 7.49 (s, 2H), 7.35 (s, 1H), 7.26 (d+s, 1H+CHCl3), 5.66 (d, 1H), 4.71 (d, 1H), 4.33 (m, 1H), 4.10 (m, 1H), 4.00 (s, 3H), 3.85 (m, 4H), 3.80 (m, 4H), 2.15 (s, 3H), 2.13 (s, 3H), 1.60 (br, 2H), 0.72 (d, 3H).

Provenance & Evidence