Electric Literature of 6214-45-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 6214-45-5 as follows.
Example 45{6-[(4-Butoxybenzyl)(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-ylamino}acetic acid(Exemplary compound No. 899)45-(a): Ethyl {6-[(4-Butoxybenzyl)(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-ylamino}acetateTo 2.5 ml of a tetrahydrofuran solution containing 158 mg (0.451 mmol) of ({6-[(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)ethyl acetate obtained in Reference example 34 were added 89.2 mg (0.495 mmol) of 4-butoxybenzyl alcohol, 169 mul (0.677 mmol) of tri-n-butylphosphine and 116 mg (0.674 mmol) of N,N,N’,N’-tetramethylazodicarboxamide, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1?1:4 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 212 mg of the title compound as colorless oily product. (Yield: 92%)Mass Spectrum (FAB, m/z): 513 (M++1).1H-NMR Spectrum (CDCl3, delta ppm): 8.60 (ddd, J=4.8, 1.7, 1.0 Hz, 1H), 7.81 (ddd, J=7.8, 1.3, 1.0 Hz, 1H), 7.74 (ddd, J=7.8, 7.6, 1.7 Hz, 1H), 7.37 (ddd, J=7.6, 4.8, 1.3 Hz, 1H), 7.23 (dd, J=8.3, 7.2 Hz, 1H), 7.20-7.16 (m, 2H), 6.79-6.73 (m, 2H), 6.49 (d, J=7.2 Hz, 1H), 6.22 (d, J=8.3 Hz, 1H), 4.71-4.65 (m, 1H), 4.68 (s, 2H), 4.36 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 3.96 (d, J=5.6 Hz, 2H), 3.92 (t, J=6.5 Hz, 2H), 1.80-1.69 (m, 2H), 1.54-1.42 (m, 2H), 1.29 (t, J=7.1 Hz, 3H), 0.97 (t, J=7.4 Hz, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6214-45-5, its application will become more common.
Reference:
Patent; UBE INDUSTRIES, LTD.; US2012/259123; (2012); A1;,
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