Related Products of 796600-15-2, 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 796600-15-2 as follows.
Example 1tra/?s-2-Chloro-4-[ [2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile, Isomer 2bsoluteIn a glass pressure vessel, a mixture of trans-2-amino-l-methyl-cyclopentanol (8.75 g, 53 mmol, 1.5 eq), 2-chloro-4-fluoro-3-methyl-benzonitrile (6 g, 35.4 mmol) and lithium carbonate (7.84 g, 106 mmol) in DMSO (72 mL) and water (7.2 mL) is degassed for 15 min by bubbling nitrogen through the mixture. The vessel is sealed and heated at 130 C for 36 h. After cooling to room temperature, the mixture is quenched over ice/water (700 mL) at 5 C (internal temperature) with stirring. After 15 min, the initially sticky solid turns into a cream solid that is collected by filtration and washed with cold water. The solid is stirred over EtOAc (100 mL) for 30 min and filtered through a pad of diatomaceous earth. The EtOAc filtrate is concentrated to afford 15 g of a yellow solid. The material is purified by silica gel chromatography using dichloromethane to elute impurities and 10%EtOAc/dichloromethane to elute final product to obtain the racemic title compound (9.2 g, 98%). 1H NMR (400 MHz, DMSO-d6) delta 7.48 (d, 1H), 6.90 (d, 1H), 5.51 (d, 1H), 4.66 (s, 1H), 3.65-3.74 (m, 1H), 2.21 (s, 3H), 2.01-2.13 (m, 1H), 1.50-1.78 (m, 5H), 1.07 (s, 3H). LC-ES/MS m/z (35C1/37C1) 265.2/267.1 (M+l). The compound is dissolved in MeOH (70 mL). The enantiomers are separated in 21 mg injections by supercritical fluid chromatography on two CHIRALPAK AD-H columns (2 x 25 cm, 5 muiotaeta) stringed in series. Mobile phase: 20% isopropanol/carbon dioxide. Flow rate: 65 mL/min. Detection: 215 nm. Each run is 6.48 min. The first eluting peak is obtained as Isomer 1 and the second eluting peak is obtained as the title compound, Isomer 2 (4.13 g, 100% enantiomeric excess). The enantiomeric excess is determined by SFC on a CHIRALPAK AD-H (4.6 x 100 mm, 5 muiotaeta) column using 20% isopropanol/carbon dioxide. Flow rate: 2.5 mL/min. Detection: 215 nm. Isomer 1 TR = 2.53 min. Isomer 2 (title compound) TR = 3.06 min.The compound of Example 1 can also be named or referred to as 2-chloro-4- [ [( 1 R,2R)-2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile.
According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.
Reference:
Patent; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (2013); A1;,
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