Sodium bis(trimethylsilyl)amide → HCID 86647081, compound

Participants

Reaction Steps

At 0° C., a solution of (R)-4-(2-fluoro-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (Example 146, Step 6) (155 mg, 0.244 mmol) and 6-chloro-5-methoxypyridin-3-amine (Small Molecules, Inc) (77 mg, 0.488 mmol) in 1 mL of THF was treated with sodium bis(trimethylsilyl)amide (0.853 mL of 1.0 M solution in THF, 0.853 mmol) and the dark red solution was stirred at that temperature for 1 h. It was quenched with 4 mL of saturated aqueous ammonium chloride solution and extracted with EtOAc (2×20 mL). The combined organic phases were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was loaded on a silica gel column and eluted with 50-100% EtOAc in DCM to give the title compound (140 mg, 74% yield) as an orange amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.11 (s, 1H), 8.70 (d, J=2.40 Hz, 1H), 8.37 (d, J=2.30 Hz, 1H), 8.18 (dd, J=8.8, 2.40 Hz, 2H), 7.28 (m, 4H), 6.90 (m, 4H), 4.85-4.81 (m, 4H), 3.87 (s, 3H), 3.74 (s, 3H), 3.70 (s, 3H), 3.60 (m, 1H), 3.04 (m, 4H), 2.78 (s, 3H), 2.59 (s, 3H), 2.47 (m, 4H), 1.34 (m, 3H). m/z (ESI, positive ion) 774.9 (M+H)+.

Provenance & Evidence