Synthetic Route of 111-95-5, These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
The [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carbaldehyde (100 mg, 0.245 mmol) obtained in Example 47, bis(2-methoxyethyl)amine (70 mg, 0.53 mmol) and acetic acid (0.029 ml, 0.51 mmol) were dissolved in 1,2-dichloroethane (5 ml). To the resulting solution was added sodium triacetoxyborohydride (115 mg, 0.515 mmol) at room temperature. The resulting mixture was stirred at room temperature for 3 days. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The resulting mixture was separated into layers. The organic layer thus obtained was washed sequentially with a satu-rated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated under reduced pressure to afford a white solid. The resulting solid was washed with hexane to give the title compound (101 mg, 0.192 mmol, 78%) as a white powder. 1H-NMR(400MHz,CDCl3) delta: 2.73(4H,t,J=5.8Hz), 3.31(6H,s), 3.47(4H,d,J=5.8Hz), 3.75(2H,s), 5.93(1H,s); 6.88-6.97(1H,m), 6.97-7.07(1H,m), 7.38(2H,d,J=8.8Hz), 7.50-7.60(3H,m), 7.76(1H,dd,J=8.1,2.0Hz), 7.98-8.08(1H,m), 8.54(1H,d,J=2.0Hz). MSm/z: 525(M++H).
Statistics shows that Bis(2-methoxyethyl)amine is playing an increasingly important role. we look forward to future research findings about 111-95-5.
Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1640366; (2006); A1;,
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