Electric Literature of 89809-65-4, 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.89809-65-4, name is Methyl 6-Cyanopyridine-3-carboxylate, molecular formula is C8H6N2O2, molecular weight is 162.1454, as common compound, the synthetic route is as follows.
To a solution of methyl 5-(3-chlorobenzyl)pyridin-2-amine (0.262 g, 1 .2 mmol) in toluene (7 ml_) was added trimethylaluminum (0.6 ml_,1 .2 mmol, 2 M in toluene) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h before a solution of methyl 6-cyanonicotinate (0.162 g, 1 mmol) in toluene (2 ml_) was added. Reaction mixture was stirred at 100 0 C for 2 h under argon. The reaction solution was cooled to room temperature and quenched with methanol (5 ml_) and 1 N hydrochloric acid aqueous (5 ml_). The volatiles were concentrated, and the aqueous phase was extracted with dichloromethane (1 00 ml_ x 2). The combined organic layers were washed with brine (1 00 ml_), dried over sodium sulfate, filtered and concentrated. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified v/a prep-HPLC (Boston C18 21 *250 mm 10 pm column. The mobile phase was acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-chlorobenzyl)pyridin-2-yl)-6-cyanonicotinamide (70 mg, 0.20 mmol, 20.8%) as a white solid. 1 H NMR (500 MHz, Dimethylsulfoxide-c/g) d 1 1 .33 (s, 1 H), 9.22 (d, J = 1 .3 Hz, 1 H), 8.53 (dd, J = 4.3, 2.5 Hz, 1 H), 8.36 (d, J = 2.0 Hz, 1 H), 8.20 (d, J = 8.0 Hz, 1 H), 8.12 (d, J = 8.5 Hz, 1 H), 7.75 (dd, J = 4.3, 2.5 Hz, 1 H), 7.35 – 7.32 (m, 2H), 7.28-7.23 (m, 2H), 3.99 (s, 2H); LCMS (ESI) m/z: 349.0 [M+H]+.
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Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
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