Reference of 179022-43-6, 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 179022-43-6 as follows.
Example 27: 8-((5-((cis-4-methylcyclohexyl)oxy)naphthalen-2-yl) azabicyclo[3.2.1]octane-3-carboxylic acid To a solution of methanesulfonic acid 5-(4-methyl-cyclohexyloxy)-naphthalen-2- ylmethyl ester (177 mg, 0.508 mmol) in DMF (2 mL), 8-aza-bicyclo[3.2.1]octane-3- carboxylic acid methyl ester HCl salt (208.38 mg, 1.0131 mmol) was added, followed by cesium carbonate (495.14 mg, 1.5197 mmol). The reaction was then heated at 80 C for lh. After cooled down, the reaction mixture was diluted with EtOAc, washed with water (2x). The organic phase was then separated, dried and concentrated. The crude was purified by HPLC, removed the solvent, the ester was then dissolved in tetrahydrofuran (2.3 mL, 29 mmol) , treated with 1.0 M of lithium hydroxide in Water(3.5 mL, 3.5 mmol) at rt overnight. Acidified with 1NHC1, the organic layer was dried and concentrated. The crude was then purified by HLPC to give 8-((5-((cis-4-methylcyclohexyl)oxy)naphthalen- 2-yl)methyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid as a white powder (132.9 mg, 64% ). LCMS: RT 1.40 min.; MH+ 408.1. 1H NMR (400 MHz, METHANOL-d4) delta 8.38 (d, J = 8.72 Hz, 1H), 7.98 (s, 1H), 7.60 (d, J = 10.48 Hz, 1H), 7.46 (d, J = 4.96 Hz, 2H), 6.92 – 7.08 (m, 1H), 4.85 (br. s., 1H), 3.80 – 4.45 (m, 2H), 3.37 (s, 2H), 1.35 -2.81 (m, 18H), 1.00 (d, J = 5.65 Hz, 3H).
According to the analysis of related databases, 179022-43-6, the application of this compound in the production field has become more and more popular.
Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; SUN, Lihong; XIN, Zhili; ZHANG, Lei; WO2014/25708; (2014); A1;,
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