Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof
A compound, pyrazole technology, applied in the field of substituted pyrazole compounds, can solve problems such as undeveloped and large population base
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Embodiment 1-12
[0115] Synthetic route 1:
[0116]
[0117] Wherein starting material acid chloride can be prepared by corresponding carboxylic acid, route is as follows:
[0118]
[0119] General synthetic method 1:
[0120] Step 1: Dissolve anhydrous acetaldehyde and a catalytic amount of anhydrous zinc chloride in dry dichloromethane (10 mL) at 0°C, then slowly add compound (C), and heat to 50°C, react for 2.5h. After the reaction was completed, 100 mL of dichloromethane was added to the reaction liquid, and then washed with saturated aqueous sodium bicarbonate (1×50 mL), the aqueous phase was extracted with dichloromethane (2×25 mL), and the organic phases were combined. The organic phase was washed successively with distilled water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain compound (B).
[0121] Step 2: Edaravone (...
Embodiment 3
[0123] The preparation of embodiment 3 isobutyric acid-1-(3-methyl-1-phenylpyrazole) oxyethyl ester
[0124]
[0125] Prepared by general synthetic method 1, a yellow oily liquid was obtained with a yield of 31.17%.
[0126] 1 H NMR (400MHz, CDCl 3 )δ7.68–7.62(m,2H),7.41(t,J=7.9Hz,2H),7.29–7.23(m,1H),6.46(q,J=5.3Hz,1H),5.58(s,1H ),2.53(dt,J=14.0,7.0Hz,1H),2.26(s,3H),1.59(d,J=5.3Hz,3H),1.14(dd,J=9.4,7.0Hz,6H).
[0127] ESI-MS(m / z):[M]+289.20
Embodiment 4
[0128] The preparation of embodiment 4 pivalic acid-1-(3-methyl-1-phenylpyrazole) oxyethyl ester
[0129]
[0130] Prepared by general synthetic method 1, a white solid was obtained with a yield of 34.28%.
[0131] 1 H NMR (400MHz, CDCl 3 )δ7.65(d, J=7.6Hz, 2H), 7.41(t, J=7.9Hz, 2H), 7.33–7.19(m, 1H), 6.45(q, J=5.3Hz, 1H), 5.57( s,1H),2.26(s,3H),1.58(d,J=5.3Hz,3H),1.16(s,9H).
[0132] ESI-MS(m / z):[M]+303.30
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