N-methyl-2-pyrrolidone → HCID 20598987, compound

Participants

Reaction Steps

This intermediate was prepared in the same manner as that of Example 109 Step A, employing carboxylic-acid from Example 66 Step,D (12.85 g; 26.6 mmol) in dry NMP (10 mL), DIEA (18.5 mL; 106.4 mmol), HOBt (8.09 g; 59.9 mmol), intermediate from Step A above (6.3 g; 33.25 mmol), and HBTU (15.1 g; 39.9 mmol). The residue resulting after workup was purified by flash column chromatography (gradient elution 45% to 50% to 55% EtOAc/hexane) to provide the desired product. 1H NMR (500 MHz, CDCl3): δ1.26 (s, 3H), 1.29 (s, 3H), 2.34 (apparent td, J=3.2, 11.7 Hz, 1H), 2.44 (dd, J=3.9, 11.7 Hz, 1H), 2.85 (d, J=10.9 Hz, 1H), 3.22-3.32 (broad, 1H), 3.66 (d, J=11.9 Hz, 1H), 3.75-4.27 (broad, 3H), 4.50 (apparent dd, J=3.7, 18.8 Hz, 1H), 4.68 (d, J=5.0 Hz, 2H), 4.82 (s, 1H), 4.88 (1/2ABX, J=6.8, 18.7 Hz, 1H), 5.28 (d, J=10.5 Hz, 1H), 5.34 (d, J=16.9 Hz, 1H), 5.90-6.00 (br s, 1H), 6.62-6.72 (br s, 1H), 7.17 (apparent t, J=8.6 Hz, 2H), 8.00 (m, 2H), 8.15-8.25 (br s, 1H); electrospray ionization mass spectrum: m/e 517.3 (MH+ calcd for C23H29F4N4O5, 517.2).

Provenance & Evidence