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ChemicalBook CAS DataBase List Selumetinib
606143-52-6

Selumetinib synthesis

2synthesis methods
Selumetinib was developed by AstraZeneca in the United Kingdom and is mainly used for the treatment of cholangiocarcinoma, colorectal cancer, and NSCLC. It can be synthesized by nitration, aminolysis, esterification, reduction, cyclization, methylation, hydrolysis and condensation from 2,3,4-trifluorobenzoic acid.
-

Yield:-

Steps:

Multi-step reaction with 7 steps
1.1: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 5 h / 30 - 35 °C
1.2: 0.75 h / 10 - 20 °C
2.1: toluene-4-sulfonic acid / acetonitrile / 2.25 h / 20 - 65 °C
2.2: 0.5 h
2.3: 0.33 h / 45 - 50 °C
3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1.17 h / 15 - 20 °C
4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 42 h / 15 - 20 °C
5.1: sodium hydroxide; water / tetrahydrofuran / 12.17 h / 25 - 30 °C
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C
6.2: 24 h / 25 - 30 °C
7.1: hydrogenchloride / water; ethanol / 24 h / 25 - 30 °C

References:

SUN PHARMACEUTICAL INDUSTRIES LIMITED;SAINI, Anil;KAZI, Muddassar Ajij;KHANNA, Mahavir Singh;PRASAD, Mohan WO2018/65924, 2018, A1

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