1,2-Dichloroethane → HCID 178494081, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 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-methylbenzoic acid (EXAMPLE 39, 195 mg, 0.276 mmol), EDC (106 mg, 0.55 mmol), HOBt (56 mg, 0.42 mmol), and DIEA (96 μl, 0.55 mmol) in DMF (2 mL) was added 5-aminotetrazole monohydrate (144 mg, 1.38 mmol). After stirring at 40° C. for 8 hours, the reaction mixture was directly applied to reverse phase HPLC, eluting with 10% to 100% acetonitrile in water, to obtain the title compound (160 mg, 57% yield), as a white solid after lyophilization. LCMS (M+H)+: 799.1. 1H NMR (DMSO-d6, 500 MHz): δ 12.44 (s, 1H), 8.31 (s, 1H), 8.28 (d, J=2.5 Hz, 1H), 8.13 (s, 1H), 8.08 (s, 1H), 7.99 (m, 1H), 7.98 (s, 2H), 7.82 (d, J=2.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 5.89 (d, J=8.5 Hz, 1H), 4.54 (d, J=17.0 Hz, 1H), 4.34 (m, 1H), 4.05 (d, J=17.0 Hz, 1H), 3.93 (s, 3H), 3.76 (m, 4H), 3.70 (m, 4H), 2.40 (s, 3H), 0.62 (d, J=6.5 Hz, 3H). RTA IC50: 11 nM

Provenance & Evidence