Triethylamine → HCID 25211713, compound

Participants

Reaction Steps

A solution of ((S)-3-Amino-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone, hydrochloride (Example 26, 79 mg, 0.20 mmol) in THF (3 mL) was treated with dimethylaminoacetyl chloride hydrochloride (40 mg, 0.24 mmol) followed by triethylamine (62 μL, 0.44 mmol). The resulting mixture was stirred for 16 hr, evaporated to an oil, and dissolved in water (3 mL). The solution was then basified with a saturated aqueous K2CO3 solution and the precipitated product filtered, washed with water, and air dried to afford product as a colorless solid (69 mg, 78%). 1H NMR (CDCl3) 1.62-1.72 (m, 2H), 1.78-1.84 (m, 1H), 1.94-2.04 (m, 1H), 2.25 (s, 6H), 2.32 (d, J=1.3, 3H), 2.49 (s, 2H), 3.24-3.40 (m, 2H), 3.94-4.04 (m, 2H), 4.12 (br d, J=13.2, 1H), 7.23 (br d, J=7.5, 1H), 7.44 (d, J=4.0, 1H), 7.47 (br s, 1H). 13C NMR 7.9, 23.5, 30.4, 45.6, 46.2, ˜51 (br), 63.2, 114.8, 118.8 (q, J=271), 128.3, 129.5, 131.6, 140.2, 155.1 (q, J=40), 157.9, 163.1, 170.7. 19F NMR −63.1. LC/MS 4.59 min, [M+1]+445.

Provenance & Evidence