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 1262407-18-0 as follows. Computed Properties of C9H16N2O2
To a solution of 4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexanone (0.30 g, 1.0 mmol) and tert-b tyl 3,6-diazabicyclo[3.1.0]hexane-3-carboxylate (0.20 g, 1.1 mmol) in DCE (5 mL) at room temperature under nitrogen was added acetic acid (0.11 mL, 2.0 mmol) and sodium triacetoxyborohydride (0.53 g, 2.5 mmol). The mixture was heated at 45 C overnight. The reaction formed a major side product (alcohol) from the ketone starting material. The mixture was quenched with saturated NaHC03 (aq.). The organic layer was separated and the aqueous layer was extracted once with DCM. The combined organic phases were concentrated under reduced pressure and purified by preparative HPLC. Pure fractions were combined, neutralized with saturated NaHC03 (aq.), and concentrated. The resulting suspension was filtered to afford the title compound as a white solid (0.026 g, 5.5%). Exact mass calculated for C23H33FN2O5S: 468.2, found: LCMS m/z = 469.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.00-1.14 (m, 2H), 1.20-1.32 (m, 1H), 1.41 (s, 9H), 1.45-1.61 (m, 2H), 1.82-2.03 (m, 5H), 2.26 (s, 2H), 3.03 (s, 3H), 3.32 (dd, J = 17.56, 11.49 Hz, 2H), 3.55 (t, J = 10.99 Hz, 2H), 3.89 (dd, J = 5.94, 1.89 Hz, 2H), 7.05 (t, J = 8.08 Hz, 1H), 7.61-7.66 (m, 1H), 7.67 (d, J = 9.35 Hz, 1H). The cis analog was also obtained as a white solid (0.052 g, 11.1%).
According to the analysis of related databases, 1262407-18-0, the application of this compound in the production field has become more and more popular.
Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; YUE, Dawei; ZHU, Xiuwen; WO2012/145361; (2012); A1;,
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