Triethylamine → 1-Acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea

Beteiligte Stoffe

Reaktionsschritte

To a solution of N,N-bis(2-chloroethyl)benzene-1,4-diamine hydrochloride (18, 0.306 g, 1.0 mmol) in dry CHCl3 (35 mL) containing Et3N (0.2 mL) was added dropwise a solution of triphosgene (115 mg, 0.4 mmol.) in an ice bath with vigorous stirring for 30 min. The reaction mixture was evaporated and the residue diluted with THF (20 mL), filtered through a pad of Celite, washed with THF (5 mL). The combined filtrate and washings (containing carbamoyl chloride 38) were then added dropwise into a solution of commercially available 9-aminoacridine hydrochloride (248 mg, 1.0 mmol) in dry DMF (10 mL) containing Et3N (0.5 mL) at room temperature. After being stirred for 16 h, the solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of CHCl3/MeOH containing silica gel (5 g) and evaporated in vacuo to dryness. The residue was put on the top of a silica gel column (2×20 cm) using CHCl3/MeOH (50/1v/v) as eluent. The fractions containing the main product were combined and evaporated in vacuo to dryness and residue was recrystallized from acetone to give 1-acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea (BO-1034); 273 mg (60%); mp 184-186° C.; 1HNMR (DMSO-d6) δ 3.71 (8H, s, 4×CH2), 6.73 (2H, d, J=9.1 Hz, 2×ArH), 7.10-7.13 (2H, m, 2×ArH), 7.28-7.53 (3H, m, 3×ArH), 7.58-7.60 (2H, m, 2×ArH), 7.84 (1H, brs, exchangeable, NH), 8.15 (2H, d, J=9.1 Hz, 2×ArH), 8.22 (1H, m, ArH), 9.37 (1H, brs, exchangeable, NH). Anal. Calcld. for (C24H22Cl2N4O); C, 63.58; H, 4.89; N, 12.36. Found: C, 63.35; H, 5.05; N, 12.09.

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