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US 10,059,653 B2Granted
Process for the preparation of indanamine derivatives and new synthesis intermediates
AssigneeOlon S.P.A.
InventorsGiorgio Bertolini, Paolangelo Cerea, Corrado Colli, Lazzaro Feliciani, Federico Gassa, Aldo Bianchi, Federica Colombo, Stefano Maiorana, Filippo Nisic
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Abstract
Subject-matter of the invention is a process for the preparation of a key intermediate in the synthesis of indacaterol. Subject-matter of the invention are also new synthesis intermediates. Formula (I):
Claims16
A process for the preparation of a compound of formula (I)
- or salts thereof, wherein R is a hydrogen atom or an amine protecting or activating group, comprising:
- (a) protecting the hydroxy of the compound of formula (II)
- to obtain the compound of formula (III)
- (b) carrying out a Friedel Crafts reaction on the compound of formula (III) to obtain the compound of formula (IV)
- (c) hydrogenating the compound of formula (IV) to obtain the compound of formula (V)
- (d) carrying out a Friedel Crafts reaction on the compound of formula (V) to obtain the compound of formula (VI)
- (e) hydrogenating the compound of formula (VI) to obtain the compound of formula (VII)
- (f) deprotecting the hydroxy of the compound of formula (VII) to obtain the compound of formula (VIII)
- (g) introducing the group of formula X to obtain the compound of formula (IX);
- (h) reacting the compound of formula (IX) with a compound of formula R—NH2 to obtain the compound of formula (I) and optionally converting it into a salt thereof, wherein R is as defined above, Pr is a protecting group of the oxygen which is not cleavable by hydrogenation and X is a leaving group for a nucleophilic substitution.
7 more elements
A process for the preparation of a compound of formula (I)
- wherein R is a hydrogen atom or an amine protecting or activating group, or a salt thereof, comprising:
- introducing the group of formula X on the hydroxy of a compound of formula (VIII)
- wherein X is a leaving group, to obtain the compound of formula (IX);
- reacting the compound of formula (IX) with a compound of formula R—NH2 to obtain the compound of formula (I) and optionally converting it into a salt thereof.
1 more element
Dependencies are inferred from the claim text.