IP Library › Granted Patent US 8,329,724
Granted Patent B2
US 8,329,724 · App. 12/843,908 · Granted Dec 11, 2012

Process for the manufacture of pharmaceutically active compounds

Assignee: Hoffmann-La Roche Inc.
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Quick Facts
Patent No.
US 8,329,724
App. No.
12/843,908
Granted
Dec 11, 2012
Kind
B2
Abstract

According to the present invention there are provided novel processes for the manufacture of the compound of formula 1 as well as novel synthesis routes for key intermediates used in those processes.

Claims (20)

1. A process for the manufacture of the compound of formula (1),

comprising the steps of reacting the compound of formula (5),

with 4-chlorophenylboronic acid in the presence of a palladium Catalyst to produce the compound of formula (6),

 and

cleaving the 2,6-dichlorobenzamide group in said compound of formula (6) to produce the compound of formula (1).

2. The process according to claim 1 , wherein the compound of formula (5) is obtained by:

reacting the compound of formula (2),

with oxalylchloride to produce the corresponding acid chloride;

reacting said acid chloride with 5-bromo-7-azaindole in the presence of aluminium trichloride to produce the compound of formula (4),

 and

reacting said compound of formula (4) with 2,6-dichlorobenzoylchloride to produce the compound of formula (5).

3. The process according to claim 1 , wherein:

(A) said compound of formula (5) is obtained by:

reacting the compound of formula (2)

with oxalylchloride in the presence of methylenechloride and N,N-Dimethylformamide to produce the corresponding acid chloride;

reacting said acid chloride with 5-bromo-7-azaindole in the presence of aluminium trichloride to produce the compound of formula (4)

 and

reacting said compound of formula (4) with dichlorobenzoylchloride in the presence of dimethylaminopyridine and n-tripropylamine to produce the compound of formula (5)

 and

(B) said cleavage of the 2,6-dichlorobenzamide group in said compound of formula (6) is accomplished by reacting said compound with ammonia in methanol or ethanol solution diluted with a polar aprotic solvent.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 31, 2010
From: HILDBRAND, STEFAN; MAIR, HANS-JUERGEN
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 024913/0426 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2010
From: REN, YI
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 024910/0045 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2010
From: F. HOFFMANN-LA ROCHE AG
To: HOFFMANN-LA ROCHE, INC.
Reel/Frame 024910/0170 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2010
From: RADINOV, ROUMEN NIKOLAEV; WRIGHT, JAMES ANDERSON
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 024919/0055 →
Priority Claims (2)
EP 09167054 · Aug 3, 2009 · regional
EP 09175101 · Nov 5, 2009 · regional
Continuity (1)
Related Publication 20110028511A1 · Feb 3, 2011