Triethylamine → HCID 57433670, compound

Participants

Reaction Steps

The racemic 4-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[piperidin-3-yl]pyrimidin-2-amine hydrochloride (70 mg g, 0.15 mmol) was dissolved in a 80/20 mixture of DCE and DMF (1.2 ml) and treated with three equivalent of triethylamine (63 uL). The 4-fluorobenzaldehyde (19 mg, 0.15 mmol) was added, followed by a 0.2 M solution of Me4NBH(OAc)3 in 80/20 DCE/DMF (1.2 ml). The mixture was stirred at room temperature for 18 hours. The mixture was washed with a 1N sodium hydroxide solution (2 ml). Concentration in vacuo followed by purification on reverse phase HPLC provides the title compound as a pale yellow solid (42.4 mg, 56%). M.p.=131-133° C. 400 MHz 1H NMR (DMSO-d6) δ: 8.73 (br. s, 1H), 8.06 (d, J=5.1 Hz, 1H), 7.64-7.58 (m, 2H), 7.44 (d, J=4.7 Hz, 1H), 7.35-7.31 (m, 2H), 7.30-7.23 (m, 2H), 7.07 (t, J=8.8 Hz, 2H), 7.00 (br. s, 1H), 6.29 (d, J=5.1 Hz, 1H), 4.00-3.90 (m, 1H), 3.49 (s, 2H), 2.96-2.90 (m, 1H), 2.69-2.62 (m, 1H), 2.08-1.94 (m, 2H), 1.93-1.85 (m, 1H), 1.76-1.67 (m, 1H), 1.61-1.48 (m, 1H), 1.42-1.30 (m, 1H). LCMS: 503 [M+H].

Provenance & Evidence