Application of 1173081-96-3 ,Some common heterocyclic compound, 1173081-96-3, molecular formula is C8H13ClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a mixture of 5-bromo-2-methyl-3-(2-methylpiperidin-1-yl)benzoic acid (250mg, 0.801 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride salt(160 mg, 0.848 mmol) and HOAt (110 mg, 0.808 mmol) in dichloromethane (DCM) (15 mL) was added N-methylmorpholine (100 )lL, 0.910 mmol), followed by EDC free base(150 mg, 0.966 mmol). The reaction was stirred at room temperature for 18 h. LCMSshowed that the reaction was complete. The reaction was concentrated under vacuum thenpurified by silica gel chromatography (Analogix, SF25-40 g, 0 to 4% MeOH in CH2Cb) togive 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(2-methylpiperidin-1-yl)benzamide (268 mg, 0.600 mmol, 75.0% yield), after trituration with20% CH2Cb in hexanes, filtration, and drying under vacuum as an off-white solid. 1HNMR (400MHz, DMSO-d6) 8 = 11.48 (s, 1 H), 8.23 (t, J= 4.9 Hz, 1 H), 7.26 (d, J= 1.8Hz, 1 H), 7.09 (d, J= 2.0 Hz, 1 H), 5.86 (s, 1 H), 4.24 (d, J= 5.1 Hz, 2 H), 3.08-2.96 (m,1 H), 2.84 ( d, J = 11.4 Hz, 1 H), 2.49 – 2.39 (m, 1 H), 2.18 (s, 3 H), 2.16 (s, 3 H), 2.11 (s, 3H), 1.81 -1.66 (m, 2 H), 1.64-1.52 (m, 2 H), 1.48-1.25 (m, 2 H), 0.77 (d,J= 6.1 Hz, 3H). MS(ES)+ m/e 446.3 [M+H]+
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1173081-96-3, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE LLC; BURGESS, Joelle, Lorraine; DUQUENNE, Celine; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; VERMA, Sharad, Kumar; WO2013/173441; (2013); A2;,
Pyridine – Wikipedia,
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