Little discovery in the laboratory: a new route for 1,1-Dioxo-isothiazolidine

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An elementary termolecular reaction involves the simultaneous collision of three atoms, molecules, or ions.26364-65-8, name is 2-Cyanoimino-1,3-thiazolidine. Here is a downstream synthesis route of the compound 26364-65-8. 26364-65-8

Into a 4 mL vial was added isothiazolidine 1,1-dioxide (9.04 mg, 0.075 mmol) and (S)-6-chloro-3-(1-(4-chloropyrimidin-2-ylamino)ethyl)quinolin-2(1H)-one IV-1 (25 mg, 0.075 mmol) in DMF (250 muL). To this solution was added Cs2CO3 (48.6 mg, 0.149 mmol) and DIEA (26.1 muL, 0.149 mmol) and the reaction mixture was stirred at 110 C. for 1.5 hours. The mixture was then diluted with EtOAc and washed with brine (*2). The organic extract was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude product. This crude material was purified by column chromatography on a Biotage chromatography system (eluted with 0-100% EtOAc in hexanes) to afford the title compound (5.2 mg, 17% yield). 1H NMR (300 MHz, CDCl3): delta ppm 8.03 (br s, 1H), 7.93 (br s, 1H), 7.61 (br s, 1H), 7.41 (br d, J=8.50 Hz, 2H), 6.70 (br s, 1H), 5.42 (br s, 1H), 4.03 (br s, 1H), 3.83 (br s, 1H), 3.46 (m, 2H), 3.38 (m, 2H), 1.55-1.71 (m, 3H). LCMS (Method 1): Rt 2.02 min, m/z 419.89[M+H]+.

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Reference£º
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R Bruce; Ashwell, Susan; Lancia, JR., David R.; Caravella, Justin Andrew; Lu, Wei; (171 pag.)US2016/83365; (2016); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com