Acetic Acid → 2-(1H-pyrazol-3-yl)-1,3-thiazole

Dissolved 1-(thiazol-2-yl)ethanone (1-BA-1, 5 g, 39.7 mmole) in DMF DMA (9.5 g, 2 eq). The resulting mixture was warmed to 100° C. until all the ketone starting material was consumed. This material was concentrated under reduced pressure to give 6.5 g of crude intermediate. This material was dissolved in 25 mL of DCM and 5 mL of HOAc was added, followed by hydrazine (5 g, 4 eq) at 0° C. The resulting mixture was heated at reflux until all the starting material was consumed. The reaction mixture was cooled to rt and neutralized with 30 mL of a saturated NaHCO3 solution. The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by MPLC (eluted with 0-20% MeOH/DCM) to give 2-(1H-pyrazol-5-yl)thiazole (Compound 2-BA-1, ˜6 g). LC/MS: 152.0 m/z (M+H)+.

1. customwas consumed
2. concentrationThis material was concentrated under reduced pressure
3. customto give 6.5 g of crude intermediate
4. temperatureThe resulting mixture was heated
5. temperatureat reflux until all the starting material
6. customwas consumed
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with DCM (2×50 mL)
9. dry with materialThe organic layers were dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe crude material was purified by MPLC (eluted with 0-20% MeOH/DCM)

ORD record

ord-edb57215d5a14a1fa828bb86aaf09c38

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445503B2