Sodium bis(trimethylsilyl)amide → HCID 178419964, compound

Participants

Reaction Steps

To a solution of 6′-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)-[3,4′]bipyridinyl-3′-ylamine (80 mg, 0.16 mmol) in anhydrous tetrahydrofuran (2 mL) was added sodium bis(trimethylsilyl)amide (1N solution in THF, 0.46 mL, 0.46 mmol) under a flow of nitrogen and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then evaporated in vacuo to afford a residue that was purified by preparative HPLC (20-60% MeCN in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min) to afford the title compound as an orange solid (10 mg, 10%). 1H NMR (DMSO-D6, 500 MHz): 12.33 (s, 1H), 9.12 (s, 1H), 8.95 (s, 1H), 8.94 (d, J=2.2 Hz, 1H), 8.88 (s, 1H), 8.31 (s, 1H), 7.80 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.0 Hz, 2H), 3.49 (s, 2H), 2.36 (s, 4H), 1.52 (m, 4H), 1.41 (m, 2H), triazole NH not observed. LCMS (Method D): RT=6.68 min, M+H+=410.

Provenance & Evidence