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 6279-86-3 as follows. Quality Control of Triethyl methanetricarboxylate
5-ethyl-6-{4-[(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-5(lH)-yl]phenyl}-4-hydroxy-2- oxo-l,2-dihydropyridine-3-carboxylic acid hydrochloride (1:1) (Cpd 246)Step 1:A solution of l-(4-chlorophenyl)butan-l-one (5.00 g, 27.37 mmol) and t-butyl amine(11.60 mL, 109.90 mmol) in DCM (30 mL) was cooled to 0 C. A solution of TiCl4 (1MDCM, 18.00 mL, 18.00 mmol) was added dropwise via syringe pump over 30 min. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was diluted with DCM (200 mL) and then the reaction was quenched with aHC03 (aqueous saturated, 60 mL). After vigorous shaking, the organic phase was separated using a PTFE phase separator, then dried over Na2S04. The solvent was removed to afford a colorless oil (5.30 g, 81), which was used directly in the next step without furtherpurification.The oil (2.14 g, 8.99 mmol) and triethylmethane tricarboxylate (2.20 mL, 10.46 mmol) in diglyme (9 mL) were heated at 160 C for 2 h. After the mixture was cooled to room temperature, a white solid was collected by filtration and washed with Et20. The resulting product (1.54 g, 53%) was obtained as a colorless crystalline material.XH NMR (500 MHz, DMSO-i?) delta ppm 0.95 (t, J=7.4 Hz, 3H) 1.30 (t, J=7.1 Hz, 3H) 2.18 (d, J=7.4 Hz, 2H) 4.34 (q, J=7.1 Hz, 2H) 7.44 (d, J=8.2 Hz, 2H) 7.57 (d, J=8.2 Hz, 2H) 11.43 (br. s., 1H) 13.57 (s, 1H). LC-MS 322.2/324.2 [M+H]+, RT 1.30 min.
According to the analysis of related databases, 6279-86-3, the application of this compound in the production field has become more and more popular.
Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33240; (2013); A1;,
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