Diisopropylethylamine → HCID 86762149, compound

Participants

Reaction Steps

A solution of 5-cyanopicolinic acid (6.65 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 12 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-(5-(5-cyanopicolinamido)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (6 mg, 0.012 mmol, 40.3% yield) as a white solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 9.90 (s, 1H), 8.94 (d, J=1.2 Hz, 1H), 8.45 (d, J=8.1 Hz, 1H), 8.24 (dd, J=8.1, 2.0 Hz, 1H), 8.10-7.97 (m, 1H), 7.72 (d, J=4.0 Hz, 1H), 7.16 (dd, J=10.7, 9.0 Hz, 1H), 4.27-4.06 (m, 2H), 3.32 (d, J=12.7 Hz, 1H), 3.04-2.84 (m, 2H), 2.49-2.34 (m, 1H), 2.23 (td, J=13.0, 7.9 Hz, 1H), 1.51 (s, 9H). MS (M+H)+: 498.20.

Provenance & Evidence