Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 149765-15-1, name is N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 149765-15-1
In a 50 mL round-bottomed flask charged with (2R,3R,4R,5R)-4-(benzyloxy)-5- ((benzyloxy)methyl)-3-fluorotetrahydrofuran-2-ol(0.31 g, 0.94 mmol), N-(4-chloro-7H- pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (0.26 g, 1.03 mmol) and Ph3P (0.54 g, 2.07 mmol) was added dry THF (5 mL) to give a colorless solution under N2. This was cooled to 0C and then DIAD (0.4 mL, 2.07 mmol) was added dropwise to give a yellow solution. After 20 min, ice- water bath was removed and after stirring for 22 hours, solvent was removed in vacuo. The crude material was purified by Si02 column chromatography eluting from hexanes/EtOAc = 6/1 to 5/1 to 4/1 to afford N-(7-((2R,3R,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3- fluorotetrahydrofuran-2-yl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (0.22 g, 41%) as a white solid. 1H NMR (400 MHz, CDC13) 58.08 (s, 1H), 7.40 – 7.24 (m, 11H), 6.47 (dd, J = 3.8, 0.4 Hz, 1H), 6.26 (dd, J = 19.6, 1.6 Hz, 1H), 5.59 (ddd, J = 53.2, 4.4, 2.0 Hz, 1H), 4.93 (ddd, J = 19.6, 8.0, 4.4 Hz, 1H), 4.83 (d, J= 11.6 Hz, 1H), 4.75 (d, J = 11.6 Hz, 1H), 4.54 (d, J = 11.6 Hz, 1H), 4.49 (d, J= 12.0 Hz, 1H), 4.37 – 4.34 (m, 1H), 3.85 (dd, J= 10.8, 2.4 Hz, 1H), 3.70 (dd, J = 10.8, 4.8 Hz, 1H), 1.33 (d, J= 0.8 Hz, 9H). HRMS C3oH32ClFN404 [M+H+]; calculated: 567.2096, found 567.2180.
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Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis, C.; PAINTER, George, R.; BLUEMLING, Gregory, R.; WO2014/124430; (2014); A1;,
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