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US 2006/0135781 A1Published application
Process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents and uses thereof
AssigneesAventis Pharmaceuticals Inc., Axys Pharmaceuticals, Inc.
InventorsJiayao Li, John Link, Colette Colladant
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Abstract
The present invention is directed to a novel process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents that are useful in the synthesis of a variety of pharmaceuticals, in particular certain cysteine protease inhibitors.
Claims8
-7. (canceled)
A process of preparing a compound of formula (VIIa):
- wherein:
- R30 is isopropylmethyl or cyclopropylmethyl which process comprises:
- (i) reacting benzoxazole with a Grignard reagent in a suitable solvent to provide a benzoxazolyl Grignard reagent;
- (ii) reacting benzoxazolyl Grignard reagent obtained in Step (i) above with an aldehyde of formula (IIa):
- where PG is an amino-protecting group to provide a compound of formula (IIIa):
- (iii) deprotecting the amino group in (IIIa) to provide a compound of formula (IVa) and optionally converting the free base to an acid addition salt;
- (iv) reacting (IVa) or its acid addition salt with a compound of formula (Va):
- where R30 is cyclopropylmethyl or isopropylmethyl, under coupling reaction conditions to provide a compound of formula (VIa):
- and;
- (v) oxidizing (VIa) with a suitable oxidizing agent to provide a compound of formula (VIIa);
- (vi) optionally converting a compound of formula (VIIa) to an acid addition salt;
- and
- (vii) optionally converting a salt form of a compound of formula (VIIa) to a free base.
10 more elements
Dependencies are inferred from the claim text.