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US 6,608,202 B1Granted
Process of synthesis of a tricyclic ketone intermediate
AssigneeSchering Corporation
InventorsHenry J. Doran, Pat M. O'Neill, Robert P. Williams
Life of this patent
Estimating the term…
Abstract
In one embodiment, the present invention describes the synthesis of a compound of Formula III, wherein X is halogen, and intermediates therefor from easily available starting materials by a simple route.
Claims20
A process of making a compound of Formula III wherein X is halogen,
- and pharmaceutically acceptable salts thereof, comprises:
- a) alkylating a compound of Formula I
- with a compound of formula Y-X, where Y is arylalkyl group, and X is a halogen, in the presence of a lithium amide and an additional base, to form an acid hydrochloride compound of Formula IIa:
- b) converting the acid hydrochloride of Formula IIa into an intermediate of Formula IIb:
- and
- c) cyclizing the compound of Formula IIb into the compound of Formula III:
- the steps b) and c) being done in one pot.
4 more elements
A process of making a compound of Formula VI:
- and pharmaceutically acceptable salts thereof, comprises:
- a) mixing a compound of Formula I:
- with a solvent comprising triethylamine, THF or a combination thereof, lithium amide and an additional base of formula M—Ot—Bu, where M is sodium or potassium;
- b) reacting the mixture of step a) with a compound of Formula IV:
- where X is Cl;
- to form an acid hydrochloride compound of Formula IIa:
- c) converting the acid hydrochloride of Formula IIa into an intermediate of Formula IIb in the presence of Vilsmeier's reagent;
- and
- d) cyclizing the compound of Formula IIb into the compound of Formula III:
- the steps c) and d) being done in one pot.
7 more elements
Dependencies are inferred from the claim text.