Preparation of an s1p receptor modulator
AssigneeOppilan Pharma Ltd.
InventorsVenkat BOLLU, James COLLINS, John NUSS, Shendong YUAN, Scott Alan WOLCKENHAUER
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Abstract
Described herein is the preparation of the SIP receptor modulator tamuzimod ((R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(tri-fluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one) and chemical intermediates used in the synthetic process.
Claims31
A process for the (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one (Compound 1), comprising:
- A) the reaction of the compounds with the structures:
- with HOBT and EDCI to produce a compound with the structure:
- B) followed by the reaction of the compounds with the structures:
- and With cesium carbonate to produce (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one (Compound 1) having the structure:
A process for the (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one (Compound 1), comprising:
- A) the reaction of the compounds with the structures:
- with potassium carbonate to produce a compound with the structure:
- B) followed by the reaction of the compound with the structure:
- with hydroxylamine to produce a compound with the structure:
- C) the reaction of the compounds with the structures:
- with HATU and DIEA to produce (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one (Compound 1) having the structure:
A process for the preparation of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one (Compound 1):
- comprising contacting the compounds with the structures:
- with a base in the presence of a solvent.
A process for the preparation of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one (Compound 1):
- comprising contacting the compounds with the structures:
- with a coupling agent and a base in the presence of a solvent.
A compound with the structure:
A compound with the structure:
Dependencies are inferred from the claim text.