Dichloromethane → 5-(3-Cyano-thiophen-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-oxadiazole

To a stirred solution of 3-cyano-thiophene-2-carboxylic acid (42.5 mg, 0.278 mmol) and methylene chloride (1.5 mL) in an ice bath under argon, was added oxalyl chloride (205 μL, 0.410 mmol) over 2 min and then 2 drops of dimethylformamide. The solution was stirred for 5 min, the ice bath was removed, and the solution was stirred for 1 h. The solution was concentrated to dryness to yield a white solid. To the solid was added 5-trifluoromethyl-pyridine-2-amidoxime (56.4 mg, 0.275 mmol) and pyridine (1.6 mL), and the resultant solution was stirred for 10 min at ambient temperature. The solution was then refluxed for 21 h. The solution was cooled to room temperature and the product was precipitated by addition of 5 mL of deionized water. The precipitate was filtered, washed with deionized water, and dried under vacuum to yield 38.3 mg (43%) of the title compound as a pink solid. 1H NMR (CDCl3): 9.09 (m, 1H), 8.40 (d, J=8.25 Hz, 1H), 8.16 (dd, J=8.24, 2.20 Hz, 1H), 7.80 (d, J=5.22 Hz, 1H), 7.52 (d, J=5.22 Hz, 1H).

1. customthe ice bath was removed
2. stirringthe solution was stirred for 1 h
3. concentrationThe solution was concentrated to dryness
4. customto yield a white solid
5. temperatureThe solution was then refluxed for 21 h
6. customthe product was precipitated by addition of 5 mL of deionized water
7. filtrationThe precipitate was filtered
8. washwashed with deionized water
9. customdried under vacuum

ORDレコード

ord-33e0ac2090bb4b73bc9ea08fa883004d

出典データセット

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07041685B2