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With n-butyllithium; sodium chloride; In tetrahydrofuran; hexane; ethyl acetate; |
(10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)-[1-(triphenylmethyl)imidazol-2-yl]methanol 50 ml of a solution of 1.32 g of 1-(triphenylmethyl)imidazole in dry tetrahydrofuran was ice-cooled in a nitrogen atmosphere. After adding 2.8 ml of a 1.6 M solution of n-butyllithium in hexane, the resulting mixture was stirred for 2 hours. Then the reaction mixture was cooled to -78° C. After adding 1.23 g of cerium (III) chloride, the reaction mixture was stirred for 30 minutes. Further, 40 ml of a solution of 0.546 g of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)carbaldehyde in dry tetrahydrofuran was dropped thereinto. Then the reaction mixture was brought back to room temperature and distributed into an aqueous solution of sodium dihydrogenphosphate and ethyl acetate. After filtering off the inorganic matters, the aqueous layer was extracted with ethyl acetate, washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate followed by filtration. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 716 mg of the title compound as a yellow solid. 1H-NMR(CDCl3) delta ppm: 2.84(d, J=8 Hz, 1H), 3.44(s, 3H), 4.98(d, J=8 Hz, 1H), 5.07(d, J=9 Hz, 1H), 5.19(d, J=9 Hz, 1H), 6.40(dd, J=2, 8 Hz, 1H), 6.68(d, J=8 Hz, 1H), 6.77(d, J=2 Hz, 1H), 6.78(d, J=2 Hz, 1H), 7.09-7.12(m, 7H), 7.23-7.26(m, 9H), 7.82(s, 2H) |
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