With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.
Example 103-[1-(5-chloro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (One Enantiomer Isolated) To a solution of 5-chloro-1,3-benzoxazole-2-thiol (0.50 g, 2.7 mmol, Aldrich) in toluene (10 mL) was added thionyl chloride (0.59 mL, 8.1 mmol) followed by a drop of DMF. The reaction was heated to reflux for 30 min and the solvent removed in vacuo. A portion of this crude product (17 mg) and 3-pyrrolidin-3-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (20.0 mg, 0.0457 mmol; enantiomer 2 from Example 9, Step 2b) were dissolved in 1,4-dioxane (0.40 mL) and N,N-diisopropylethylamine (16 microL, 0.091 mmol) was added. The mixture was heated to 70 C. for 1.5 h. The solvent was removed in vacuo and the residue was sequentially stirred with 50% TFA/DCM for 1.5 h, concentrated, then stirred with 0.3 mL EDA in methanol for 30 min. Purification via preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) afforded product. 1H NMR (400 MHz, d6-DMSO): delta 12.13 (br s, 1H), 8.88 (s, 1H), 8.68 (s, 1H), 8.43 (s, 1H), 7.60 (d, 1H), 7.41 (d, 1H), 7.31 (d, 1H), 7.02-6.97 (m, 2H), 4.86 (dt, 1H), 3.86 (dd, 1H), 3.68-3.59 (m, 1H), 3.54-3.28 (m, 4H), 3.03-2.90 (m, 1H), 1.77-1.67 (m, 2H); LCMS (M+H)+: 459.0, 461.0.
22876-19-3 5-Chlorobenzo[d]oxazole-2(3H)-thione 708870, abenzoxazole compound, is more and more widely used in various.
Reference£º
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem