反应详情

[(2-Nitrophenyl)methyl](4-(3-pyridyl)(1,3-thiazol-2-yl)amine was prepared according to the method described in Example 16 (Step b) by employing amino{[(2-nitrophenyl)methyl]amino}methane-1-thione (1.03 g, 4.9 mmol) (Example 16, Step a), 3-(bromoacetyl)pyridine hydrobromide (Aust. J. Chem. 1989, 42, 1735; 1.37 g, 4.9 mmol), and 50% MeOH (50 mL). The crude yellow oil, iron dust (Aldrich) (1.39 g, 24.9 mmol) and NH4Cl (198 mg, 3.7 mmol) in 50% EtOH (50 mL) was heated at reflux. After 1 h the solvent was removed in vacuo. The residue was dissolved in THF (20 mL) and to this solution was added 4-nitrophenyl chloroformate (Aldrich) (860 mg, 4.2 mmol) followed by Et3N (0.85 mL, 6.1 mmol) and the reaction was heated at reflux. After 1 h the reaction was cooled to RT and stirred overnight. The solvent was removed in vacuo and purified by flash chromatography on silica gel with Hexanes:EtOAc (1:1) to CH2Cl2:MeOH (39:1, 19:1) as eluant to give an off-white solid. Mp: 269–272° C. MS m/z: 309 (M+1). Calc'd for C16H12N4OS—308.07.

1. temperatureat reflux
2. customAfter 1 h the solvent was removed in vacuo
3. dissolutionThe residue was dissolved in THF (20 mL) and to this solution
4. temperaturethe reaction was heated
5. temperatureat reflux
6. customThe solvent was removed in vacuo
7. custompurified by flash chromatography on silica gel with Hexanes:EtOAc (1:1) to CH2Cl2:MeOH (39:1, 19:1) as eluant
8. customto give an off-white solid