Hydrochloric Acid → HCID 22479931, compound

Triphenylphosphine (1.31 g, 5.00 mmol), THF (4.00 mL), 3-N,N-dimethylaminopropanol (0.592 mL, 5.00 mmol) and diethylazodicarboxylate (0.788 mL, 5.00 mmol) were added to 3-(4-hydroxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.400 g, 1.25 mmol). The mixture was stirred at ambient temperature for 15.5 h and poured into aqueous 6 N hydrochloric acid (30 mL). After stirring at ambient temperature for 4 h, the mixture was extracted with ethyl acetate (3×). The aqueous fraction was added to aqueous 6 N NaOH (30 mL) and the pH adjusted to 11. The solution was extracted with ethyl acetate (3×) and the organic fractions were combined and dried over anhydrous sodium sulfate, filtered and evaporated. Purification by flash chromatography on silica gel pretreated with 2% triethylamine/hexanes followed by 0–20% ethyl acetate/hexanes, sonication of the product in ethyl acetate (3 mL), addition of hexanes (20 mL) and filtration gave the title compound (0.206 g, 51% yield). ES-MS (m/z) 321 [M+1]+

1. stirringAfter stirring at ambient temperature for 4 h
2. extractionthe mixture was extracted with ethyl acetate (3×)
3. additionThe aqueous fraction was added to aqueous 6 N NaOH (30 mL)
4. extractionThe solution was extracted with ethyl acetate (3×)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customPurification by flash chromatography on silica gel
9. customfollowed by 0–20% ethyl acetate/hexanes, sonication of the product in ethyl acetate (3 mL)
10. additionaddition of hexanes (20 mL) and filtration

ORD record

ord-2497b2642abe4c89a61cc2debe7317ff

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220771B2