反应详情

A solution of 4 (170 mg, 0.62 mmol) in dry ethanol (15 mL) was treated with 5 (0.355 g, 1.24 mmol) and stirred for overnight (17 h) at room temperature. The reaction mixture was diluted with saturated NaHCO3 solution (100 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic fractions were washed with brine (50 mL), dried (Na2SO4) and concentrated. The crude product was purified by dry column chromatography (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2 3:97) to give compound 45 (177 mg, 74%) as a yellow solid. 1H-NMR (DMSO-d6) δ: 1.38-1.69 (m, 8H), 1.83-1.89 (m, 2H), 2.02-2.12 (m, 2H), 2.19 (s, 3H), 2.65-2.68 (m, 2H), 2.80-3.12 (m, 5H), 6.32 (brs, 2H), 6.62-6.64 (m, 2H), 6.85-6.88 (d, 1H, J=8.9 Hz), 7.06-7.09 (t, 1H, J=3.8 Hz), 7.56-7.58 (d, 1H, J=5.0 Hz), 7.69-7.71 (d, 1H, J=3.6 Hz); ESI-MS (m/z, %): 383 (MH+, 33), 192 (100), 142 (51). ESI-HRMS calculated for C22H30N4S (MH+), calculated: 383.2253; observed: 383.2263; HPLC-purity: 93.49% by area.

1. extractionextracted with CH2Cl2 (2×50 mL)
2. washThe combined organic fractions were washed with brine (50 mL)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated
5. customThe crude product was purified
6. dry with materialby dry column chromatography (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2 3:97)