8-(4-氨基苯基)-5-甲基-N-丙基-1,3-二氧杂环戊烯并[4,5-G]酞嗪-6(5H)-甲酰胺

步骤一,制备4-(4-乙酰基氨基苯基)-1,2-二氢-1-甲基-2-丙基氨基甲酰基-6,7-甲基二氧邻苯二甲酰肼
将4-(4-乙酰氨基苯基)-1,2-二氢-1-甲基-6,7-甲基己二氧基邻苯二甲腈(0.10g,0.31mmol)溶于二氯甲烷(5mL),搅拌下用异氰酸丙酯(0.5mL)处理.5小时后,再添加异氰酸丙酯(0.5mL),并将混合物搅拌48小时.用氮气流将溶剂吹干,并将残余物在硅胶上进行色谱分离,用33%己烷/ EtOAc至25%己烷/ EtOAc的梯度洗脱.所得产物为浅黄色泡沫状固体(108mg,86%).
200 MHz 1 H NMR (CDCl 3); δ 7.63 (ABq, 4H, J = 9.4 Hz, ArH'), 7.40 (bs, 1H, ArNH), 6.77 (s, 1H, ArH), 6.74 (s, 1H, ArH), 6.62 (t, 1H, J = 8.5 Hz, NHCH2), 6.02 (s, 2H, ℃H2O), 5.71 (q, 1H, J = 10.9 Hz, CHCH3), 3.33 (dt, 1H, J = 8.5 Hz, J = 7.8 Hz, NHCHCH2), 2.18 (s, 3H, C℃H3), 1.61 (q, 2H, J =7.8 Hz, CH2CH2CH3), 1.27 (d, 3H, J = 10.9 Hz, CHCH3), 0.98 (t, 3H, J = 7.8 Hz, CH2CH3).
步骤二,制备8-(4-氨基苯基)-5-甲基-N-丙基-1,3-二氧杂环戊烯并[4,5-G]酞嗪-6(5H)-甲酰胺
将4-(4-乙酰基氨基苯基)-1,2-二氢-1-甲基-2-丙基氨基甲酰基-6,7-甲基二氧邻苯二甲酰肼(0.10g,0.25mmol)溶于含有1N氢氧化钠(4mL)的甲醇(8mL)溶液,并加热回流72小时. 将溶液冷却至环境温度,用EtOAc(30mL)稀释,并用水(30mL)洗涤. 用EtOAc(25mL)萃取水层,并将合并的有机层干燥(MgSO 4)并真空蒸发. 将粗产物在硅胶上进行色谱分离,用50%己烷/ EtOAc洗脱,得到纯产物,为浅黄色泡沫状固体(75mg,82%).
200 MHz 1 H NMR (CDCl 3); δ 7.41 (d, 2H, J = 6.5 Hz, ArH), 6.81 (s, 1H, ArH), 6.77 (d, 2H, J = 6.5 Hz, ArH), 6.71 (s, 1H, ArH), 6.00 (s, 2H, ℃H2O), 5.67 (q, 1H, J = 6.7 Hz, CHCH3), 3.85 (brs, 2H, NH2), 3.30 (dt, 2H, J = 8.3 Hz, J = 6.2 Hz, NHCH2CH2) , 1.58 (m, 2H, CH2CH2CH3), 1.24 (d, 3H, J = 6.7 Hz, CHCH3), 0.95 (t, 3H, J = 7.5 Hz, CH2CH3).
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