Tyramine → HCID 11045887, compound

Participants

Reaction Steps

A solution of tyramine (302 mg, 2.3 mmol) and DIEA (299 mg, 2.3 mmol) in DMF (5 mL) was added dropwise to a DMF solution (5 mL) of 2,4-dichloro-6-{[3-(4-fluorophenyl)propyl]methylamino}-1,3,5-triazine (prepared in 92% yield via the procedure outlined for the preparation of Intermediate 13, using N-[3-(4-fluorophenyl)propyl]-N-methylamine, Intermediate 5), (714 mg, 2.3 mmol) in DMF (10 mL). The resulting solution was stirred at RT for 2 h. The solvent was removed under reduced pressure and the resulting residue was diluted with EtOAc (80 mL) and washed with 10% aqueous citric acid (2×40 mL). The organic layer was dried over sodium sulfate and concentrated to give the title compound (950 mg, 100%) as a white solid which was used without further purification: 1H NMR (CDCl3, 400 MHz) δ 7.27-6.94 (m, 6H), 6.75 (m, 2H), 5.40-5.32 (d, br, 1H) 3.72-3.56 (m, 4H), 3.11 (m, 3H), 2.78 (m, 2H), 2.62 (m, 2H), 1.92 (m, 2H); Low resolution MS (ES+) m/e 416.4 (MH+). Intermediate 22: tert-butyl 4-(4-{[3-(4-chlorophenyl)propyl]sulfanyl}-6-{[2-(4-hydroxyphenyl)ethyl]amino}-1,3,5-triazin-2-yl)-1-piperazinecarboxylate

Provenance & Evidence