反应详情

A mixture of 3-chlorophenacyl bromide (467 mg, 2 mmol) and (3-morpholin-4-yl-propyl)-thiourea (407 mg, 2 mmol) in dry ethanol (4 ml) was heated at reflux for 2 min, cooled to room temperature, and concentrated in vacuo. The resulting residue was suspended in dichloromethane (5 mL) followed by the addition of N,N-diisopropylethylamine (554 μL, 3 mmol) and thiophene-2-carbonyl chloride (160 μL, 1.5 mmol). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (3 mL) and subjected to HPLC purification (Method Y). The resulting free amine was dissolved in MeOH (2 mL) and 1M HCl/ether (75 mL) was added. The precipitate was filtered and dried in vacuo to provide the title compound (367 mg) as an off-white solid as the hydrochloride salt. LC/MS (ESI) m/z 447.9 [M+H]. HPLC retention time (Method A)=2.95 min.

1. temperaturewas heated
2. temperatureat reflux for 2 min
3. concentrationconcentrated in vacuo
4. temperatureThe reaction mixture was maintained at room temperature overnight
5. concentrationconcentrated in vacuo
6. dissolutionThe resulting residue was dissolved in DMSO (3 mL)
7. customsubjected to HPLC purification (Method Y)
8. dissolutionThe resulting free amine was dissolved in MeOH (2 mL)
9. addition1M HCl/ether (75 mL) was added
10. filtrationThe precipitate was filtered
11. customdried in vacuo