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1. (WO1998049148) PREPARATION OF MIBEFRADIL II

Pub. No.:    WO/1998/049148    International Application No.:    PCT/EP1998/002415
Publication Date: Fri Nov 06 00:59:59 CET 1998 International Filing Date: Fri Apr 24 01:59:59 CEST 1998
IPC: C07D 235/14
Applicants: F. HOFFMANN-LA ROCHE AG
Inventors: HARRINGTON, Peter, John
WONG, Jim-Wah
Title: PREPARATION OF MIBEFRADIL II
Abstract:
A method of preparing 2-[2-{[3-(1H-benzimidazol-2-yl) propyl]methyl-amino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4- tetrahydronaphthalen-2-yl methoxyacetate comprises contacting (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4- tetrahydronaphthalen-2-yl)acetic acid or an activated derivative of (6-fluoro-2-hydroxy-1- isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid with [3-(1H- benzimidazol-2-yl)propyl]methylamine to form N-[3-(1H-benzimidazol-2-yl) propyl]-2-(6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl) -N-methylacetamide, reducing this to 2-[2- {[3-(1H-benzimidazol-2-yl)propyl]methylamino}ethyl] -6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-ol, and treating the 2-[2- {[3-(1H-benzimidazol-2-yl)propyl]methylamino} ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen -2-ol with methoxyacetic acid or an activated derivative of methoxyacetic acid.