Triethylamine → HCID 24863631, compound

Participants

Reaction Steps

A 25-mL round bottom flask was charged with 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(1-(2,4-dichloro-5-methoxyphenyl)piperidin-4-yl)ethanamine (23 mg, 0.047 mmol), anhydrous DCM (2 mL), and triethylamine (0.016 mL, 0.118 mmol). The resultant solution was treated with methanesulfonyl chloride (5.50 μL, 0.071 mmol) and stirred at RT for 1 h. After this time, the mixture was concentrated on a rotary evaporator, and the resultant residue was partitioned between EtOAc and saturated sodium bicarbonate. The organic phase was washed with brine, dried (MgSO4) and concentrated to give the crude product. The crude product was purified by flash chromatography (4 g silica gel cartridge, EtOAc/hexanes) to afford Example 4 g (22 mg, 0.039 mmol, 82% yield). LC-MS: 563.0 (M+H); tR=4.18 min (method c). 1H-NMR (400 MHz, CDCl3) δ ppm 7.16 (1 H, s), 6.49 (1 H, s), 4.59 (1 H, d, J=9.23 Hz), 4.20-4.26 (1 H, m), 4.09-4.15 (1 H, m), 3.76-3.81 (3 H, m), 3.59 (1 H, d, J=6.15 Hz), 3.30-3.39 (2 H, m), 2.65 (3 H, s), 2.48-2.54 (2 H, m), 2.23-2.32 (3 H, m), 1.91 (1 H, s), 1.75-1.81 (1 H, m), 1.55-1.62 (2 H, m).

Provenance & Evidence