HRID1434894

反应详情

EQUATION

反应方程式

HRID 1434894 的结构方程式

PROCEDURE

实验过程

This example describes the synthesis of compounds 7 and 8 of FIG. 5. A solution of 2-dimethylamino-4-(3-indolyl)imidazole 5.HCl (0.2 g, 0.76 mmol) in 40 mL of methanol saturated with ammonia (MeOH, sat. NH3) was allow to stir in the presence of air at 25° C. for 1 day during which time compound 7 precipitated from the solution as a dark solid and was collected by filtration. Resubjection of 7 to an ammonia saturated methanol solution in air for 7 days at 25° C. produced compound 8 as a orange solid after concentration of the reaction mixture in vacuo followed by Flash silica gel chromatography (CH2Cl2/MeOH(NH3), 19:1). The yield of compound 8 was 60%. Referring to FIGS. 21 and 22, Compound 7: 1H NMR (300 MHz, DMSO-d6) δ 11.98 (bs, 2H), 10.43 (s, 2H), 8.72 (m, 2H), 7.49 (m, 2H), 7.22 (m, 4H), 3.46 (bs, 6H); 13CNMR (100 MHz, DMSO-d6) δ 173.2 (sx2), 172.1 (sx2), 147.2 (sx2), 139.5 (dx2), 137.6 (sx2), 128.2 (sx2), 124.6 (dx2), 123.6 (dx2), 122.0 (dx2), 112.8 (dx2), 111.9 (sx2), 38.9 (qx4); HRFABMS calcd for C26H25N8 449.2202, found 449.2178. Referring to FIGS. 23-25, Compound 8: 1H NMR (300 MHz, DMSO-d6) δ 13.36 (s, 1H), 12.13 (s, 1H), 11.88 (bs, 1H), 11.00 (bs, 1H), 9.03 (d, J=7.7 Hz, 1H), 8.94 (bs, 1H), 7.96 (bs, 1H), 7.68 (dm, J=7.7 Hz, 1H), 7.55 (m, 2H), 7.42-7.28 (m, 3H), 3.37 (s, 6H); 13C NMR (100 MHz, DMSO-d6+D2O) δ 167.5 (s), 155.8 (s), 148.1 (s), 143.3 (d), 141.0 (s), 138.2 (s), 134.4 (s), 130.5 (s), 128.9 (d), 128.3 (d), 125.5 (d), 125.2 (s), 124.9 (d), 124.5 (d), 121.4 (d), 120.6 (d), 118.2 (s), 114.5 (d), 112.0 (d), 108.6 (s), 103.4 (s), 40.4 (qx2); HRFABMS calcd for C23H20N7 394.1780, found 394.1784.

WORKUP

后处理

  1. customprecipitated from the solution as a dark solid
  2. filtrationwas collected by filtration