反应详情

A solution of 7-amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.125 g, 0.531 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.3 g, 1.062 mmol) at room temperature and stirred overnight (18 hours). At this time, additional methyl thiophene-2-carbimidothioate hydroiodide (0.3 g, 1.062 mmol) was added, and stirring was continued for another 24 hours. The reaction was diluted with saturated NaHCO3 solution (20 mL), and the product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layers were washed with brine (15 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2) to obtain the title compound 5 (0.16 g, 88%) as a solid. 1H NMR (DMSO-d6) δ 2.19 (s, 6H), 2.43 (t, 2H, J=6.9 Hz), 3.97 (t, 2H, J=6.9 Hz), 4.58 (s, 2H), 6.48-6.58 (m, 4H), 7.06-7.14 (m, 2H), 7.60 (d, 1H, J=5.1 Hz), 7.74 (d, 1H, J=3.3 Hz); ESI-MS (m/z, %): 345 (MH+, 100), 128 (85); ESI-HRMS calculated for C17H21N4O2S (MH+), calculated: 345.1379; observed: 345.1384; HPLC-purity: 93.15% by area.

1. stirringstirring
2. waitwas continued for another 24 hours
3. extractionthe product was extracted into CH2Cl2 (2×20 mL)
4. washThe combined CH2Cl2 layers were washed with brine (15 mL)
5. dry with materialdried (Na2SO4)
6. customThe solvent was evaporated
7. customthe crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2)