Synthesis of Triazolopyrimidine Compounds
AssigneeLek Pharmaceuticals D.D.
InventorsNenad Maras, Ivana Gazic Smilovic, Damjan Sterk
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Abstract
The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.
Claims20
A process for the preparation of a compound of formula XI or a salt thereof
- comprising the steps of:
- (i) contacting a compound of formula VI or a salt thereof
- with a compound of formula VII or VII′
- to obtain a compound of formula VIII or VIII′, respectively
- (ii) optionally, if a compound of formula VIII′ is obtained, reducing the compound of formula VIII′ to a compound of formula VIII,
- (iii) converting a compound of formula VIII by nitrosation to a compound of formula IX or a compound of formula IX′
- and
- (iv) coupling the compound of formula IX or IX′ with a compound of formula X
- or a salt thereof in a presence of a base to provide a compound of formula XI or a salt thereof.
A compound of the following formula III or a salt thereof
- wherein R1 is Boc, Cbz, TFA, Tr, TCA, CHO, Ac, Bz, Fmoc, C4-C5-tent-alkyl, or mono, di- or triphenyl substituted methyl, and R2 is Bn, t-Bu, TBDMS, MOM, Tr, Ac or Bz.
A compound of the following formula IV or a salt thereof
- wherein R1′ is hydrogen, Boc, Cbz, TFA, Tr, TCA, CHO, Ac, Bz, Fmoc, C4-C5-tent-alkyl, or mono, di- or triphenyl substituted methyl, and R2 is Bn, t-Bu, TBDMS, MOM, Tr, Ac or Bz.
A compound of the following formula V or a salt thereof
- wherein R2 is Bn, t-Bu, TBDMS, MOM, Tr, Ac or Bz.
A compound of the following formula K or a salt thereof
- wherein R1″ is H, Boc, Cbz, TFA, TCA, CHO, Ac, Bz, Fmoc, and R2 is H, Bn, t-Bu, TBDMS, MOM, Tr, Ac or Bz.
A compound of the following formula L or a salt thereof
- wherein R1″ is H, Boc, Cbz, TFA, TCA, CHO, Ac, Bz, Fmoc, and R2 is H, Bn, t-Bu, TBDMS, MOM, Tr, Ac or Bz.
A compound of the following formula VIII or VIII′
A compound of the following formula IX or IX′
Dependencies are inferred from the claim text.