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US 8,138,180 B2Granted
Exo-selective synthesis of himbacine analogs
AssigneeSchering Corporation
InventorsTiruvettipuram K. Thiruvengadam, Anantha Sudhakar, Ngiap Kie Lim, Daw-long Kwok, George G. Wu, Tao Wang, Mingsheng Huang, Michael D. Green
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Abstract
This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists. The chemistry disclosed herein is exemplified in the following synthesis sequence:
Claims2
A process for preparing Compound 3A:
- wherein R11 is unsubstituted alkyl, R12 is halogen, and n is 1, comprising:
- (a) reducing Compound 7
- to Compound 7A′:
- wherein R15 and R16 are each independently selected from the group consisting of H, unsubstituted alkyl or phenyl, or, when taken together with the nitrogen to which they are attached, form a morpholine ring;
- (b) hydrolyzing Compound 7A′ to yield Compound 15:
- (c) aminating Compound 15 to yield Compound 4:
- wherein R10 and R11 are H;
- (d) converting Compound 4 to Compound 17:
- (e) converting Compound 17 to Compound 18:
- (f) converting Compound 18 to Compound 3A:
7 more elements
Dependencies are inferred from the claim text.