Dicyclohexylcarbodiimide → Nitrogen mustard derivative 1

Beteiligte Stoffe

Reaktionsschritte

To a stirred methylene chloride solution (20 ml) was added DMAP (438 mg, 3.59 mmol) and 2-(4-(bis(2-chloroethyl)amino)phenyl)acetic acid (B-5) (906 mg, 3.27 mmol). Subsequently, DCC (690 mg, 3.35 mmol) was added to reaction mixture, followed by addition of 5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-amine (Intermediate CY-200) (800 mg, 2.97 mmol). The mixture was stirred at r.t for 24 h. After removing dicyclohexylurea (DCU) by filtration, the filtrate was concentrated in vacuum and dried over Na2SO4. The residue was purified by silica gel chromatography eluting with CH2Cl2: EtOAc=20:1 to afford total product (1.2 g, 76%) as a gray solid. LC-MS: (M+H)+=528. 1H NMR (300 MHz, CDCl3) δ 10.17 (s, 1H), 7.28-7.30 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.69 (d, J=8.7 Hz, 2H), 6.58 (s, 1H), 3.95 (s, 2H), 363-3.79 (m, 10H), 1.26 (s, 9H).

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