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ChemicalBook CAS DataBase List Regorafenib monohydrate
1019206-88-2

Regorafenib monohydrate synthesis

1synthesis methods
Among several published synthesis, the most likely process scale synthesis will be highlighted from the two published syntheses, and this is described in the scheme. Commercially available picolinic acid (148) was heated with thionyl chloride to provide the crude intermediate 4-chloro-2- pyridyl acid chloride which was subsequently reacted with aqueous methyl amine in toluene to give 4- chloro-2-methylcarboxamide as its hydrochloride salt 149 in quantitative yield after treatment with acetyl chloride in toluene and ethanol. The hydrochloride salt was free based with sodium hydroxide and then immediately reacted with imine 150 (formed upon exposure to 4-amino-3-fluorophenol (153) in refluxing 3-methyl 2-butanone) in base to provide diaryl ether 151 in 84% yield. Reaction of amine 151 with the commercially available isocyanate 152 ultimately delivered regorafenib hydrate (XXIII) in 83% yield.

755037-03-7 Synthesis
Regorafenib

755037-03-7
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Regorafenib monohydrate

1019206-88-2
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Yield:-

Reaction Conditions:

with water in acetoneProduct distribution / selectivity;

Steps:

1.1
400 mg of 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N- methylpyridine-2-carboxamide in the polymorph I, prepared as described in WO 2005/009961, are dissolved in acetone and the solution is filtered. Water is added to one fourth of the filtrate until precipitation. The precipitate is filtered and dried at room temperature under ambient humidity. The sample is tested gravimetrically and corresponds to the title compound.

References:

BAYER HEALTHCARE AG WO2008/43446, 2008, A1 Location in patent:Page/Page column 19

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