Trifluoroacetic acid → HCID 59504642, compound

Participants

Reaction Conditions

Reaction Steps

To a mechanically stirred solution of piperidine (24 mg, 0.28 mmol) in DMF (1.5 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 11.3 mg, 0.28 mmol), and the mixture was stirred at 0° C. for 30 min. 3-[4-(Bromomethyl)phenyl]-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Intermediate LL, 100 mg, 0.24 mmol) was added, and the mixture was stirred at rt over night whereupon it was directly subjected to preparative HPLC (RP-18 column; acetonitrile/water gradient containing 0.1% trifluoroacetic acid). The product-containing fractions were combined and the solvent was partly removed. A neutral pH was established by adding saturated aqueous sodium bicarbonate solution, and the mixture was extracted three times with ethyl acetate (20 mL each). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (62 mg, 61%): 1H-NMR (400 MHz, DMSO-d6) δ 8.01 (d, 2H), 7.50 (d, 2H), 7.17 (d, 2H), 7.12 (d, 2H), 6.90 (s, 1H), 5.42 (s, 2H), 3.50 (s, 2H), 2.42-2.30 (m, 4H), 2.32 (s, 3H), 2.28 (s, 3H), 1.55-1.47 (m, 4H), 1.44-1.35 (m, 2H); ES-MS m/z 428 (MH)+; HPLC RT (Method K) 1.10 min.

Provenance & Evidence