Acetic Acid → HCID 178509256, compound

Temperature

70 °C

In a 150 mL sealed tube, added 2-(2-chloropyridin-3-yl)-3-oxopropanenitrile (2.5 g, 14 mmol), water (2.0 mL, 14 mmol), acetic acid (14 mL, 14 mmol), ethanol (28 mL, 14 mmol), 1,4-dioxane (14 mL), and anhydrous hydrazine (0.40 ml, 14 mmol). The mixture was stirred at 70° C. for 20 minutes. The reaction was cooled to RT and concentrated. The concentrate was extracted into EtOAc, washed 1×NaHCO3, 1×H2O, dried over Mg2SO4, filtered through fritted funnel and concentrated. The crude was purified using reverse phase chromatography. The product was extracted into CH2Cl2 washed 1×NaHCO3 1×H2O, dried with Na2SO4, filtered through fritted funnel, concentrated to yield 4-(2-chloropyridin-3-yl)-1H-pyrazol-3-amine as tan solid. MS m/z=195 [M+1]+. Calc'd for C8H7ClN4: 194.62.

1. customIn a 150 mL sealed tube
2. temperatureThe reaction was cooled to RT
3. concentrationconcentrated
4. extractionThe concentrate was extracted into EtOAc
5. washwashed 1×NaHCO3, 1×H2O
6. dry with materialdried over Mg2SO4
7. filtrationfiltered through fritted funnel
8. concentrationconcentrated
9. customThe crude was purified
10. extractionThe product was extracted into CH2Cl2
11. washwashed 1×NaHCO3 1×H2O
12. dry with materialdried with Na2SO4
13. filtrationfiltered through fritted funnel
14. concentrationconcentrated

ORD record

ord-3f3baf3803ee4b9d99f3a00fd7e2cf4d

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242961B2