ChemicalBook CAS DataBase List Encorafenib (LGX818)

Encorafenib (LGX818) synthesis

14synthesis methods

Product Name:Encorafenib (LGX818)
CAS Number:1269440-17-6
Molecular formula:C22H27ClFN7O4S
Molecular Weight:540.01

Encorafenib, also known as LGX-818, is an orally available Raf kinase inhibitor with potential antineoplastic activity. LGX818 specifically inhibits Raf kinase, a serine/threonine enzyme in the RAF/mitogen-activated protein kinase kinase (MEK)/extracellular signal-related kinase (ERK) signaling pathway. By inhibiting the activation of the RAF/MEK/ERK signaling pathway, the administration of LGX818 may result in a decrease in proliferation of tumor cells. Synthetic Description Reference: Huang, Shenlin; Jin, Xianming; Liu, Zuosheng; Poon, Daniel; Tellew, John; Wan, Yongqin; Wang, Xing; Xie, Yongping. Preparation of sulfonamidophenylimidazolylpyrimidine derivatives and analogs for use as protein kinase inhibitors. Assignee IRM LLC, Bermuda; Novartis A.-G. WO 2011025927. (2011).

Synthetic Routes

ROUTE 1

Reference: Huang, Shenlin; Jin, Xianming; Liu, Zuosheng; Poon, Daniel; Tellew, John; Wan, Yongqin; Wang, Xing; Xie, Yongping. Preparation of sulfonamidophenylimidazolylpyrimidine derivatives and analogs for use as protein kinase inhibitors. Assignee IRM LLC, Bermuda; Novartis A.-G. WO 2011025927. (2011).

1996-30-1 Synthesis

1996-30-1
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$5.00/1g

1269440-17-6
144 suppliers
$50.00/1mg

Yield:-

Steps:

Multi-step reaction with 7 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
1.2: -78 - 20 °C
2.1: diphenylphosphoranyl azide; triethylamine / toluene / 2 h / 75 - 84 °C
2.2: 0.25 h / 35 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 16 h / 100 °C
4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 16 h / 80 °C
5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C
6.2: pH 6 - 6.5
6.3: 0.17 h / 20 °C / pH 7 - 7.5
7.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C
7.2: pH 6 - 6.5
7.3: pH 8.5

References:

IRM LLC;NOVARTIS AG;HUANG, Shenlin;JIN, Xianming;LIU, Zuosheng;POON, Daniel;TELLEW, John;WAN, Yongqin;WANG, Xing;XIE, Yongping WO2011/25927, 2011, A1

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