Dimethylformamide → HCID 21345162, compound

Participants

Reaction Conditions

Reaction Steps

2,6-DiFluoro-3-hydroxypyridine from Example 116a (2g, 15.26 mmole), 1-Cbz-2-(S)-azetidinemethyl tosylate (5.73 g 15.26 mmole, prepared in example 105), and KOH (1.4 g 24.9 mmole) were combined in DMF (15 mL) and heated at 90° C. for one hour, cooled to 20° C. and poured into brine (100 mL). The resulting mixture was extracted with ether. The combined Et2O extracts were washed with 50% brine and dried (MgSO4). The solvent was evaporated in vacuo and the crude product was chromatographed (silica gel; hexane/EtOAc 95:5 to 6:4) to yield 1.75g (34%) of the title compound. 1H NMR (DMSO-d6, 120° C. 300 MHz) δ: 2.22 (m, 1H), 2.42 (m, 1H), 3.85-3.90 (m, 2H), 4.23 (m, 1H), 4.40 (m, 1H), 4.54 (m, 1H), 5.01 (s, 1H), 6.93 (dd, J=3.0, 5.5, 1H), 7.29 (m, 5H), 7.77 (m, 1H).MS (DCI/NH3) m/e 335 (M+H)+, 352 (M+NH4)+. Anal. calcd. for C17H16F2N2O3,: C 61.07 H, 54.82 N, 8.38 Found: C, 61.10 H, 4.84; N, 7.90.

Provenance & Evidence