Diisopropylethylamine → HCID 86762154, compound

Participants

Reaction Steps

A solution of 3-fluoropicolinic acid (6.34 mg, 0.045 mmol), tert-butyl ((4aS,7aS)-7a-(5-amino-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (11 mg, 0.030 mmol), HATU (17.07 mg, 0.045 mmol), and Hunig's Base (10.46 μL, 0.060 mmol) in DMF (299 μL) was stirred at rt for 10 h. The crude product was purified by reverse phase preparative HPLC on a Luna C18 column (10 μM, 30×100 mm) eluting with 0-100% B (A: 95% eater/5% MeCN/10 nM NH4OAc, B: 5% water/95% MeCN/10 mM NH4OAc) over 12 min to give tert-butyl ((4aS,7aS)-7a-(2-fluoro-5-(3-fluoropicolinamido)phenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (6 mg, 0.012 mmol, 40.9% yield) as a white solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 9.91 (br. s., 1H), 8.49 (br. s., 1H), 8.11-7.97 (m, 1H), 7.71 (d, J=5.2 Hz, 1H), 7.68-7.61 (m, 1H), 7.61-7.55 (m, 1H), 7.17-7.10 (m, 1H), 4.27-4.06 (m, 2H), 3.33 (d, J=13.4 Hz, 1H), 3.03 (d, J=13.7 Hz, 1H), 2.90 (dd, J=13.0, 4.5 Hz, 1H), 2.47-2.33 (m, 1H), 2.29-2.15 (m, 1H), 1.51 (s, 9H). MS (M+H)+: 491.19.

Provenance & Evidence