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With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24h;
A solution of diphenylcyanocarboimidate (10 g, 42 mmol) in 168 mL CH2CI2 was treated with <strong>[15205-15-9]2-chloro-6-fluorobenzylamine</strong> (6.7 g, 42 mmol) and diisopropylethylamine (7.3 mL, 42 mmol). The reaction mixture was stirred at room temperature for 24 hr. The solvent was removed by reduced pressure and the remaining white solid was diluted with CH2Cl2and H20 and extracted 3x with CH2CI2. The organic layers were combined and the solvent removed by reduced pressure yielding a crude white solid. This intermediate (12.8 g, 42 mmol) was dissolved in 80 mL acetonitrile and treated with piperidine (6.2 mL, 63 mmol). The reaction was heated to reflux for 24 hr. The reaction mixture was cooled and the solvent removed by reduced pressure. The crude product was triturated with ether and collected by filtration to yield a white solid (10 g, 82ouzo yield) :'H NMR (CDCI3, 400 MHz) 7.28-7. 23 (m, 1 H), 7.22-7. 18 (m, 1 H), 7.04-6. 98 (m, 1 H), 4.94-4. 85 (m, 1 H), 4.68-4. 63 (m, 2H), 3.45-3. 39 (m, 4H), 1. 65-1. 57 (m, 6H); MS (ESP+) m/e 295 (MH+) ; Analytical CHN.
1-cyano-3-(isoquinolin-6-yl)-2-phenylisourea[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
32.9 mg
In tetrahydrofuran; for 3.5h;Reflux;
86.63 mg diphenyl cyanocarbonimidate, 52.1 mg <strong>[23687-26-5]isoquinolin-6-amine</strong>, and 6 ml THF were added to a reaction bottle with thermal reflux for 3.5 hrs. After removing THF by vacuum, the residue was added to 10 ml EA. The precipitated solid was filtered to obtain 32.9 mg 1-cyano-3-(isoquinolin-6-yl)-2-phenylisourea. The intermediate was reacted with equivalent tert-butyl-2-(benzylamino)ethylcarbamate and 20 mg of DIPEA in 5 ml DMF at 110 C. for 18 hrs. After cooling, 1N NaOH was added and extracted twice with EA. After the combined EA layer was dried and concentrated by Na2SO4, 26.4 mg intermediate product was eluted out by a SiO2 column (EA/Hexane 4:1). The intermediate was added to 1.5 ml 6N HCl at room temperature with stirring overnight. After the reaction solution was evaporated under reduced pressure, 2 ml acetone/methanol (10:1) was added. The precipitate was filtered and washed with acetone, and then the solid was taken and evaporated in vacuum to give 18.7 mg of product.
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