Trifluoroacetic acid → HCID 58293600, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(4-(2-methylpyridin-3-yloxy)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)piperidine-1-carboxylate from Example 116C (56 mg, 0.13 mmol) in 4 mL methylene chloride was added 4 mL of trifluoroacetic acid. The resulting mixture was stirred at room temperature for 1 h and then was concentrated in vacuo. The residue was taken up in 4 mL of methylene chloride and then there was added triethylamine (0.054 mL, 0.38 mmol) and isopropylchloroformate (0.13 mL of a 1M solution in toluene, 0.13 mmol). The resulting mixture was allowed to stir at room temperature for 18 h. The reaction was diluted with ethyl acetate, washed with sat'd aq sodium bicarbonate and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated. The residue was purified by silica gel chromatography (12 g ISCO cartridge, 0-100% ethyl acetate/hexane) to afford 28 mg (49%) of Example L16 as an off-white solid. 1H NMR (500 MHz, CDCl3) δ ppm 1.21 (d, J=6.05 Hz, 6H) 1.55-1.61 (m, 2H) 2.37 (s, 3H) 2.80-2.93 (m, 4H) 4.20-4.36 (m, 2H) 4.85-4.92 (m, 1H) 5.57 (s, 1 Ft) 6.70 (d, J=9.35 Hz, 1H) 7.21 (dd, J=7.97, 4.67 Hz, 1H) 7.40 (d, J=6.60 Hz, 1H) 8.02 (d, J=9.35 Hz, 1H) 8.42 (d, J=4.95 Hz, 1H) 8.46 (s, 1H). LRMS (ESI): 424.3 [M+H]+.

Provenance & Evidence