Benzisoxazole compound and application thereof
A compound, isoxazole technology, applied in the field of medicine, can solve problems affecting the DA function of the substantia nigra-striatum and tubercle-infundibulum system
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Embodiment 1
[0052] Example 1: 3-{1-[3-(3,4-dihydro-2H-chromen-7-yloxy)propyl]pyridin-4-yl}-6-fluorobenzo[d]isox Preparation of azole
[0053] 2.82g (0.011mol) of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride, 2.27g (0.01mol) of 7-(3-chloropropoxy)chroman mol), 5.29g (0.04mol) of anhydrous potassium carbonate and 0.17g (0.001mol) of potassium iodide were mixed in a 250mL round bottom flask, and 120mL of acetone was added as the reaction solvent, and heated to reflux for 24h. TLC monitoring showed that the reaction was complete and the product was single. Cool to room temperature, filter, wash the filter cake with acetone, combine the washing liquid with the filtrate, and concentrate to obtain a light yellow oil, which is separated by silica gel column chromatography, petroleum ether: ethyl acetate (v:v=1:2) to recover the reaction raw material 7-(3-Chloropropoxy)chroman. Ethyl acetate: triethylamine (v:v=100:1) to collect the target product. Concentration gave 2.25 g of wh...
Embodiment 2
[0054] Example 2: Preparation of 6-{3-[4-(6-fluorobenzo[d]isoxazol-3-yl)pyridin-1-yl]propoxy}chroman-4-one
[0055] According to the method of Example 1, a white solid was obtained with a yield of 54.5%, mp.135-136°C. 1 H-NMR (CDCl 3 ,600MHz)δ(ppm):7.33(1H,d,J=3.0Hz),7.25(1H,s),7.10(1H,d,J=3.0Hz),7.08(1H,d,J=3.0Hz) ,6.92(1H,d,J=9.0Hz),4.50(2H,t,J 1 =J 2 =6.6Hz), 4.05(2H,t,J 1 =J 2 =6.0Hz), 2.80(4H,m), 2.20(6H,m); ESI-MS: m / z425([M+H] + ),446.9([M+Na] + );IR,ν(cm -1 ):2952,2824,2773,1675,1613,1519,1434,1346,1282,1234,1122,1037,957,849,786,709.
Embodiment 3
[0056] Example 3: Preparation of 7-{3-[4-(6-fluorobenzo[d]isoxazol-3-yl)pyridin-1-yl]propoxy}chroman-4-one
[0057] According to the method of Example 1, a white solid was obtained with a yield of 59.7%, mp.122-123°C. 1 H-NMR (CDCl 3 ,600MHz)δ(ppm):7.83(1H,d,J=9.0Hz),7.70(1H,s),7.24(1H,q,J 1 =8.4Hz,J 2 =2.4Hz),7.05(1H,m,J 1 =8.4Hz,J 2 =8.4Hz,J 3 =2.4Hz),6.59(1H,q,J 1 =8.4Hz,J 2 =2.4Hz),6.43(1H,d,J=2.4Hz),4.51(2H,t,J 1 =J 2 =6.6Hz), 4.09(2H,t,J 1 =J 2 =6.6Hz), 3.08(3H,s), 2.75(2H,t,J 1 =J 2 =6.6Hz), 2.57(2H,s), 2.21(2H,m), 2.07(4H,m), 2.04(2H,m); ESI-MS: m / z425([M+H] + ),446.9([M+Na] + );IR,ν(cm -1 ):2957,2917,2849,2759,1675,1612,1578,1518,1495,1441,1257,1233,1197,1169,1122,1059,957,907,830,620.
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