Stereoselective synthesis of intermediate for preparation of heterocyclic compound
AssigneesTaiGen Biotechnology Co., Ltd., TaiGen Biopharmaceuticals Co.(Beijing), Ltd.
InventorsWen-Chang Chen, Han-Pei Hsu, Shan-Yen Chou, Shih-Chieh Chuang, Chi-Feng Yen
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Abstract
Provided is a stereoselective synthesis of an intermediate for the preparation of the heterocyclic derivative as a Cap-dependent endonuclease inhibitor. The synthesis process has the advantages of simple operation, higher yield and relatively controllable steroselectivity, such that it is suitable for large-scale production.
Claims15
A compound represented by formula (I) below or a salt thereof,
- wherein R1 is halogen;
- R1′ is halogen;
- and “*” stands for an R-enantiomer or an S-enantiomer.
A compound represented by the formula (II) below or a salt thereof,
- wherein R1 is halogen;
- R1′ is halogen;
- R2 is hydrogen, deuterium, halogen, or C1-C6 alkyl;
- R3 is hydrogen, NO, or NH2;
- m is 0, 1, 2, or 3;
- P is a protecting group;
- and “*” stands for an R-enantiomer, an S-enantiomer or a racemate.
A process of preparing a compound of formula (Ia) below:
- or a salt thereof, wherein R1 is halogen, and R1′ is halogen,
- the process comprising conducting a condensation reaction by contacting a compound of formula (I-1) below:
- with (S)—C1-6 alkylsulfinamide or (S)-(−)-methylbenzylamine unsubstituted or substituted with one or more groups comprising halogen or C1-3 alkyl to form the compound of formula (Ia) or the salt thereof.
A process of preparing a compound of formula (IIa-1) below:
- or a salt thereof, wherein R1 is halogen;
- is halogen;
- R2 is hydrogen, deuterium, halogen, or C1-C6 alkyl;
- m is an integer of 0, 1, 2, or 3;
- and P is a protecting group, the process comprising:
- reacting a compound of formula (I-2) below with a compound of formula (Ia) below:
- to form the compound of formula (IIa-1) or the salt thereof.
Dependencies are inferred from the claim text.