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A process for preparing (S)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4- d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one

IP.com Disclosure Number: IPCOM000238343D
Publication Date: 2014-Aug-19
Document File: 2 page(s) / 29K

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A process for preparing (S)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-
d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one

(S)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1- yl)piperidin-1-yl)prop-2-en-1-one, referred to as Compound I, has the following structure:

    Compound I may be used for preparing (S)-1-(3-(4-amino-3-(4- phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one.

Described herein below, is a process for preparing compound I:

Procedure:
(S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (compound A) (or a salt thereof) is combined with compound B (for example:3- Chloropropionyl Chloride, 3-Bromopropionyl Chloride) in organic solvent selected from the group consisting: ethers, amides, esters, nitriles, sulfoxide, ketones, hydrocarbons, acetate and halogenated hydrocarbon at a temperature of (-) 10oC- 50oC with or without the presence of a base selected from a group consisting: organic base, inorganic base, aqueous solution of organic base, to obtain Compound C. Compound C is then treated with an organic base such as triethylamine (TEA) and 1,8-Diazabicycloundec-7-ene (DBU) or with inorganic base such as tBuOK, KOH.


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The reaction can be carried out in a solvent selected from a group consisting: ethers, amides, esters, nitriles, sulfoxide, ketones, hydrocarbons, acetate and halogenated, to give compound I.