Reference of 15258-73-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.15258-73-8, name is (2,6-Dichlorophenyl)methanol, molecular formula is C7H6Cl2O, molecular weight is 177.03, as common compound, the synthetic route is as follows.
To a solution of 2,6-dichlorobenzyl alcohol (26 mg, 0.15 mmol) in tetrahydrofuran (1.5 mL) was added sodium hydride (95%, 25 mg, 1.0 mmol, 24 eq) and the reaction was stirred at 23 C for 15 minutes before adding a solution of r-(3-chloro-4-(dimethylcarbamoyl)phenyl)-[4,4′- bipiperidine]-l-carbonyl chloride (1-10) (60 mg, 0.15 mmol, 1.0 eq) in dichloromethane (1.5 mL). The resulting reaction was stirred at 23C for 16 hours. The reaction mixture was then quenched with water (0.25 mL) and concentrated and the residue was dissolved in DMSO and purified by reverse phase liquid chromatography (Gemini -NX CI 8, 5 muiotatauiota, 30 x 100 mm column; 0-100% CH3CN/H2O gradient w/ 0.10% TFA present) to yield 2,6-dichlorobenzyl l’-(3-chloro- 4-(dimethylcarbamoyl)phenyl)-[4,4′-bipiperidine]-l-carboxylate (1-11). 1H NMR (400 MHz, CD30D): delta 7.44 (s, 1 H); 7.42 (s, 1 H); 7.34 (dd, J = 9.0, 7.1 Hz, 1 H); 7.25 (d, J = 8.5 Hz, 1 H); 7.20 (d, J = 2.3 Hz, 1 H); 7.13 (dd, J = 8.6, 2.3 Hz, 1 H); 5.36 (s, 2 H); 4.21-3.98 (br m, 2 H); 3.78 (d, J = 12.4 Hz, 2 H); 3.09 (s, 3 H); 2.95 (t, J = 12.0 Hz, 2 H); 2.89 (s, 3 H); 2.77 (t, J = 12.8 Hz, 2 H); 1.89 (d, J = 12.1 Hz, 2 H); 1.74 (br s, 2 H); 1.40-1.33 (m, 4 H); 1.17 (br s, 2 H). LRMS m/z (M+H) 552.3 found, 552.2 required
The chemical industry reduces the impact on the environment during synthesis 15258-73-8, I believe this compound will play a more active role in future production and life.
Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn, J.; BENNETT, David Jonathan; BRNARDIC, Edward, J.; LIVERTON, Nigel, J.; MANLEY, Peter, J.; MENG, Zhaoyang; NANDA, Kausik, K.; RUDD, Michael, T.; WAI, Jenny; (137 pag.)WO2017/83219; (2017); A1;,
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