ChemicalBook CAS DataBase List Filgotinib

Filgotinib synthesis

9synthesis methods

Product Name:Filgotinib
CAS Number:1206161-97-8
Molecular formula:C21H23N5O3S
Molecular Weight:425.5

The synthesis of Filgotinib is as follows:
With cyclopropanyl chloride in an amidated reaction in a system consisting of N-methylmorpholine and 1,4-dioxane,The amidation reaction time was 4 h,The amidation reaction temperature was 50 ° C,The molar ratio of the intermediate (III), cyclopropanyl chloride, N-methylmorpholine and 1,4-dioxane was 1: 2.8: 2.5:TLC plate to determine the reaction is completed, cooled to room temperature,Adding methylene chloride and water, separating the organic phase with water,Then washed with brine, dried over magnesium sulfate,Evaporated to dryness and the residue was purified over a silica gel column [elution solvent: ethyl acetate / n-hexane (3: 7 v / v)To obtain a solid yellowish solid,That is, Filgotinib, yield 91.2%.
synthesis of Filgotinib.png

1257705-09-1 Synthesis

[1,2,4]Triazolo[1,5-a]pyridin-2-amine, 5-[4-[(1,1-dioxido-4-thiomorpholinyl)methyl]phenyl]-

1257705-09-1
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4023-34-1 Synthesis

4023-34-1
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1206161-97-8
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Yield:1206161-97-8 91.2%

Reaction Conditions:

with 4-methyl-morpholine in 1,4-dioxane at 50; for 4 h;Green chemistry;Reagent/catalyst;Solvent;Temperature;

Steps:

3.F F) Preparation of Filgotinib:
The intermediate (III) obtained in step E)With cyclopropanyl chloride in an amidated reaction in a system consisting of N-methylmorpholine and 1,4-dioxane,The amidation reaction time was 4 h,The amidation reaction temperature was 50 ° C,The molar ratio of the intermediate (III), cyclopropanyl chloride, N-methylmorpholine and 1,4-dioxane was 1: 2.8: 2.5:TLC plate to determine the reaction is completed, cooled to room temperature,Adding methylene chloride and water, separating the organic phase with water,Then washed with brine, dried over magnesium sulfate,Evaporated to dryness and the residue was purified over a silica gel column [elution solvent: ethyl acetate / n-hexane (3: 7 v / v)To obtain a solid yellowish solid,That is, Filgotinib, yield 91.2%The reaction of this step is the same as in Example 1.

References:

Suzhou Fushilai Pharmaceutical Co., Ltd.;Mo Guoning CN104987333, 2017, B Location in patent:Paragraph 0039; 0040; 0047; 0054; 0061

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39093-93-1 Synthesis