Intermediate products, methods for their preparation and use thereof
AssigneeBiotage AB
InventorsJacob Westman, Ronny Lundin
Life of this patent
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Abstract
Novel solid supported intermediate products of the general formula 1 coupled to a solid polymeric support through one or both of the R1 groups or through the R4 group which are suitable for synthesis of heterocyclic compounds are disclosed. Methods for preparing such intermediate products are also disclosed and also the use of the intermediate products in simple and fast methods on solid phase for synthesis of heterocycles.
Claims14
An intermediate product suitable for synthesis of heterocyclic compounds which is a compound of the general formula I
- 11
- coupled to a solid polymeric support through one or both of the R1 groups or through the R4 group
- wherein when coupled to the polymeric support through R1
- the R1 groups represent the same or different groups chosen from lower alkyl with 1 to 6 carbon atoms, such as methyl, ethyl, cycloalkyl with 3 to 6 carbon atoms in the ring, such as cyclopentyl, cyclohexyl, heterocyclic compounds including one or more heteroatoms, benzyl groups;
- two R1 groups together can be included in heterocyclic ring containing one or more nitrogen atoms;
- R2 represents H or a lower alkyl with 1 to 6 carbon atoms, such as methyl;
- R4 represents unsubstituted or substituted aromatic ring(s), unsubstituted or substituted heteroaromatic ring(s) with one or more heteroatoms, or OR5;
- when R4 is unsubstituted or substituted aromatic ring(s), unsubstituted or substituted heteroaromatic ring(s), R3 represents H, alkyl, unsubstituted or substituted aromatic ring, unsubstituted or substituted heteroaromatic ring with one or more heteroatoms, or COOR5;
- when R4 is OR5, R3 is CN, COOR5, NCOR5, NCOOR5 or COR5;
- the R5 groups, which can be the same or different, represent H, alkyl, benzyl, unsubstituted or substituted aromatic ring(s), unsubstituted or substituted heteroaromatic ring(s) with one or more heteroatoms;
- and wherein when coupled to the polymeric support through R4
- R1 and R2 are as defined above,
- R3 is as defined above except COOR5 and COR5
- R4=OR5 where R5 is as defined above except H.
Use of an intermediate product for synthesis of heterocyclic compounds which is a compound of the general formula I
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- coupled to a solid polymeric support through one or both of the R1 groups or through the R4 group,
- wherein when coupled to the polymeric support through R1,
- the R1 groups represent the same or different groups chosen from lower alkyl with 1 to 6 carbon atoms, such as methyl, ethyl, cycloalkyl with 3 to 6 carbon atoms in the ring, such as cyclopentyl, cyclohexyl, heterocyclic compounds including one or more heteroatoms, benzyl groups;
- two R1 groups together can be included in a heterocyclic ring containing one or more nitrogen atoms;
- R2 represents H or a lower alkyl with 1 to 6 carbon atoms, such as methyl;
- R4 represents unsubstituted or substituted aromatic ring(s), unsubstituted or substituted heteroaromatic ring(s) with one or more heteroatoms or OR5;
- when R4 is unsubstituted or substituted aromatic ring(s), unsubstituted or substituted heteroaromatic ring(s), R3 represents H, alkyl, unsubstituted or substituted aromatic ring, unsubstituted or substituted heteroaromatic ring with one or more heteroatoms or COOR5;
- when R4 is OR5, R3 is CN, COOR5, NCOR5, NCOOR5 or COR5;
- the R5 groups, which can be the same or different, represent H, alkyl, benzyl, unsubstituted or substituted aromatic ring(s), unsubstituted or substituted heteroaromatic ring(s) with one or more heteroatoms;
- and wherein when coupled to the polymeric support through R4
- R1 and R2 are as defined above,
- R3 is as defined above except COOR5 and COR5,
- R4=OR5 where R5 is as defined above except H,
- wherein the solid supported intermediate compound of the general formula I is reacted with a dinucleophile, i.e. a substance with two nucleophilic atoms selected from N, C, O and S adjacent to each other or separated by one or more carbon atoms, by reacting the intermediate compound and the dinucleophilic substance for a short period of time which after evaporation of the solvent produces the desired heterocyclic compound in high yield and in high purity.
Dependencies are inferred from the claim text.