Diisopropylethylamine → HCID 86762150, compound

Participants

Reaction Steps

A solution of (±)-tert-butyl (4aR,7aR)-7a-(5-amino-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate from step G of Preparation 1 (9 mg), 5-cyanopicolinic acid (6 mg), HATU (14 mg), and DIEA (11 μL), in DMF (0.12 mL) was stirred at rt for 2 h, and the crude reaction mixture was subjected to preparative HPLC eluting with 0-100% B (A: 95% H2O/5% MeCN, 10 mM NH4OAc; B: 5% H2O/95% MeCN, 10 mM NH4OAC over 12 min period to give the title compound as a white foam (5 mg, 41%). 1H NMR (500 MHz, CDCl3) δ 9.90 (1H, s), 8.94 (1H, s), 8.45 (1H, d, J=8.0 Hz), 8.24 (1H, dd, J=2.0, 8.5 Hz), 8.03 (1H, m), 7.72 (1H, m), 4.10-4.25 (2H, m), 3.32 (1H, m), 3.02 (1H, m), 2.90 (1H, m), 2.42 (1H, m), and 2.23 (1H, m) and 1.51 (9H, s). MS (M+H)+: 498.2.

Provenance & Evidence