Acetic Acid → 2-(1H-pyrazol-3-yl)-1,3-thiazole
반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=O)[CH3:7].C[N:10]([CH:12]=O)C.CC([N:17](C)C)=O.CC(O)=O.NN>C(Cl)Cl>[NH:17]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[CH:7][CH:12]=[N:10]1[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=O)[CH3:7].C[N:10]([CH:12]=O)C.CC([N:17](C)C)=O.CC(O)=O.NN>C(Cl)Cl>[NH:17]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[CH:7][CH:12]=[N:10]1Dissolved 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)+.
불러오는 중…
