Reference of 294190-18-4,Some common heterocyclic compound, 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, molecular formula is C9H10ClNO2, 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.
[01783] Step 1 : Synthesis of methyl 3-(((l r,4r)-4-((tert- butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate[01 784] To a stirred solution of methyl 3-amino-5-chloro-2-methyl benzoate (5.0 g, 25 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (6.95 g, 32.6 mmol) in 25 ml of dichloroethane, was added acetic acid (9.0 mL, 450.75 mmol) at room temperature. The reaction mixture was cooled and sodium triacetoxyborohydride (22.8 g, 108 mmol) was added and the mixture stirred at room temperature overnight. The mixture was neutralized with sat. NaHC03 and extracted with DCM. The combined organic phases were dried over a2S04, concentrated under reduced pressure and the product isomers separated by silica gel (100-200) column chromatography to give the less polar as m-isomer, methyl 3-((( l s,4s)-4-((tert- butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate (5.2 g, 52%) and the more polar title compound /rara-isomer, methyl 3-(((l r,4r)-4-((tert- butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate (3.5 g, 35%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-5-chloro-2-methylbenzoate, its application will become more common.
Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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