Diisopropylethylamine → HCID 24963708, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-piperidin-4-ylidene-methyl-phenoxy)-5-cyanopyridine trifluoroacetate (0.280 g, 0.72 mmol) and phenyl pyridin-3-ylcarbamate (0.154 g, 0.72 mmol) in DMSO (2.0 mL) was treated with diisopropylethylamine (0.170 g, 1.6 mmol) and heated to 60° C. After 3 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (5% of 1N NH3 in MeOH, in dichloromethane) to afford the title compound (155 mg, 52%) as white crystals after trituration in diethyl ether. MS (APCI 10V) AP+ 412.16; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (t, J=5.46 Hz, 2H) 2.45 (t, J=5.46 Hz, 2H) 3.46 (t, J=5.46 Hz, 2H) 3.54 (t, J=5.46 Hz, 2H) 6.39 (s, 1H) 7.02-7.04 (m, 2H) 7.12 (d, J=7.60 Hz, 1H) 7.21 (d, J=8.20, Hz, 1H) 7.25-7.27 (m, 1H) 7.39 (t, J=8.01 Hz, 1H) 7.83 (dd, J=5.28 Hz, 2.74 Hz, 2H) 8.10 (d, J=2.86 Hz, 1H) 8.25 (s, 1H) 8.30 (s, 1H) 8.8 (m, 1H) 8.75 (s, 1H).

Provenance & Evidence