Electric Literature of 68327-04-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 68327-04-8 as follows.
2,6-Difluoro-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile (3 g, 9.51 mmol), (1S,2S)-2-hydroxycyclopentylamine hydrochloride (1.96 g, 14.3 mmol), and diisopropylethylamine (2.46 g, 19 mmol) are combined in DMSO (12 mL) and stirred at 60 C. for 4 h to give 2-fluoro-6-((1S,2S)-2-hydroxy-cyclopentylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile. The mixture is then diluted with isopropanol (10 mL) and treated three times with 25% aqueous NaOH (1.5 mL) and 30% aqueous hydrogen peroxide (1 mL). The mixture is then partitioned between EtOAc (100 mL) and water (100 mL), and the aqueous layer is washed with additional EtOAc (100 mL). The combined organic layers are concentrated, and the oily residue is purified via chromatography (elution 30 to 100% EtOAc in hexanes). The clean fractions are combined, concentrated and recrystallized from EtOAc/hexanes to give 2-fluoro-6-((1S,2S)-2-hydroxycyclopentylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)benzamide (3.53 g, 89%) as a white crystalline solid. LCMS m/z=415 [M+H]-. 1H NMR (400 MHz, d6 DMSO): delta 7.72 (br s, 1H), 7.68 (br s, 1H), 7.38 (d, 1H), 6.72 (d, 1H), 6.61 (dd, 1H), 4.91 (d, 1H), 3.84 (m, 1H), 3.50 (m, 1H), 2.94 (2d, 2H), 2.38 (s, 3H), 2.31 (2 d, 2H), 2.15 (m, 1H), 1.57-1.82 (m, 3H), 1.36 (m, 1H), 1.02 (s, 3H), 1.00 (s, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,68327-04-8, its application will become more common.
Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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