Triethylamine → HCID 69239419, compound

Participants

Reaction Steps

To a solution of Example 17D (1.38 g, 4.38 mmol) in anhydrous dichloromethane (25 mL) was added triethylamine (0.9 mL) followed by 3-cyanobenzoyl chloride (0.727 g, 4.38 mmol) and the mixture was stirred for 4 hours at room temperature. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (50 mL) and H2O (20 mL). The aqueous layer was extracted with ethyl acetate (2×30 mL) and the combined organic layers dried (Na2SO4), filtered, and concentrated to an oil which was chromatographed on a Biotage 40M eluting with 10% hexane/90% ethyl acetate to provide the titled compound. MS (ESI) m/e 445 (M+H)+, 443 (M−H)−; 1H NMR (300 MHz, CD3OD) δ ppm 1.39 (s, 6 H) 1.45 (s, 3 H) 1.65 (m, 1 H) 2.53 (m, 2 H) 3.05 (m, 1 H) 3.19 (m, 2 H) 3.46 (m, 2 H) 3.78 (m, 2 H) 4.61 (m, 3 H) 7.66 (t, 1 H) 7.89 (d, 1 H) 8.11 (d, 1 H) 8.17 (s, 1 H).

Provenance & Evidence