1-Hydroxybenzotriazole → HCID 178494080, 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-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoic acid (EXAMPLE 36, 167 mg, 0.232 m mol), EDC (90 mg, 0.464 m mol), HOBt (60 mg, 0.437 m mol), and DIEA (81 μl, 0.464 m mol) in DMF (2 mL) was added 5-aminotetrazole monohydrate (120 mg, 1.16 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 get the title compound (121 mg, 43% yield), as a white solid after lyophilization. LCMS (M+H)+: 787.2. 1H NMR (DMSO-d6, 500 MHz): δ 12.44 (s, 1H), 8.31 (s, 1H), 8.29 (d, 3.5 Hz, 1H), 8.12 (s, 1H), 8.09 (s, 1H), 8.00 (m, 3H), 7.82 (d, 2.0 Hz, 1H), 7.50 (d, 8.0 Hz, 1H), 5.91 (d, 8.5 Hz, 1H), 5.59 (m, 1H), 4.53 (d, 17.0 Hz, 1H), 4.49-4.38 (m, 3H), 4.22-4.07 (m, 3H), 3.93 (s, 3H), 2.40 (s, 3H), 0.64 (d, 6.5 Hz, 3H). RTA IC50: 10 nM.

Provenance & Evidence