New learning discoveries about 58249-69-7

The synthetic route of 58249-69-7 has been constantly updated, and we look forward to future research findings.

58249-69-7,58249-69-7, 5,6-Dimethoxybenzo[d]thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

LDA (2.0M in THF, 0.6lmL, l.22mmol) was added dropwise to a mixture of 5,6- dimethoxybenzo[d]thiazole (200mg, l.02mmol) in THF (5.0mL) at -78C under N2. The reaction mixture was stirred at -78C for 1 hour. A mixture of succinic anhydride (l23mg, l.22mmol) in THF (2.0mL) was then added dropwise to the reaction mixture at -78C. The reaction mixture was warmed to RT and stirred for 2 hours. A solution of sat aq NH4Cl (l.OmL) and H20 (5.0mL) were then added to the reaction mixture. The reaction mixture was extracted with EtOAc (3x30mL). The organic layers were combined, washed with brine (20mL), dried over MgS04, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (eluting ACN in H20 with 0.1% TFA) to afford 4-(5,6-dimethoxybenzo[d] thiazol-2-yl)-4-oxobutanoic acid. LCMS (CI3HI4N05S) (ES, m/z): 296 [M+H]+. ‘ H NMR (400 MHz, DMSO-ri6) d 7.76 (s, 1H), 7.75 (s, 1H), 3.89 (s, 3H), 3.88 (s, 3H), 3.40-3.34 (m, 2H), 2.67- 2.63 (m, 2H).

The synthetic route of 58249-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CASH, Brandon, D.; CUMMING, Jared, N.; DEMONG, Duane, E.; HAIDLE, Andrew, M.; JEWELL, James, P.; LARSEN, Matthew, A.; LU, Min; OTTE, Ryan, D.; TAOKA, Brandon, M.; TROTTER, Benjamin Wesley; TRUONG, Quang, T.; (97 pag.)WO2019/195063; (2019); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 58249-69-7

58249-69-7 5,6-Dimethoxybenzo[d]thiazole 12269882, athiazole compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.58249-69-7,5,6-Dimethoxybenzo[d]thiazole,as a common compound, the synthetic route is as follows.

5,6-dimethoxybenzo[d]thiazole (l.58g, 8.09mmol) was added to a sealed tube and back evacuated with N2 (2x). THF (40mL) was added, and the reaction mixture was cooled to -78C. rt-BuLi (1.5M in Hex, 5.6mL, 8.9mmol) was added, and the reaction mixture was stirred at -78C for 30 min. 3-methyldihydrofuran-2,5-dione (l.02g, 8.90mmol) was added, and the reaction mixture was allowed to warm to RT over a period of 4 hours. HC1 (1N) was added until the aqueous layer was pH ~ 4. The aqueous layer was then extracted with EtOAc (3x). The organic layers were combined, dried over MgS04, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (eluting ACN/H20 with 0.05% TFA). The fractions containing all product isomers were combined, diluted with H20, and extracted with EtOAc (3x). The organics were combined, dried over MgS04, filtered, and concentrated under reduced pressure. The racemic mixture was resolved by Chiral-SFC (CHIRACEL OJ-H (250mmx2lmm), 25% MeOH in C02) to afford four peaks. Concentration of the third eluting peak afforded 4-(5,6-dimethoxy-l,3-benzothiazol-2-yl)-2-methyl-4- oxobutanoic acid. LCMS (CI4HI6N05S) (ES, m/z): 310 [M+H]+. 1H NMR (500MHz, MeOD- d4) d 7.65 (s, 1H), 7.59 (s, 1H), 3.96 (s, 3H), 3.97 (s, 3H), 3.69 (dd, =l8Hz, 8.8Hz, 1H), 3.28 (dd, =l8Hz, 5.5Hz, 1H), 3.15-3.08 (m, 1H), 1.33 (d, =7.3Hz, 3H)., 58249-69-7

58249-69-7 5,6-Dimethoxybenzo[d]thiazole 12269882, athiazole compound, is more and more widely used in various fields.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CASH, Brandon, D.; CUMMING, Jared, N.; DEMONG, Duane, E.; HAIDLE, Andrew, M.; JEWELL, James, P.; LARSEN, Matthew, A.; LU, Min; OTTE, Ryan, D.; TAOKA, Brandon, M.; TROTTER, Benjamin Wesley; TRUONG, Quang, T.; (97 pag.)WO2019/195063; (2019); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica