C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 295/155 (2006.01) C07C 227/26 (2006.01) C07C 229/38 (2006.01) C07D 295/092 (2006.01) C07D 333/56 (2006.01) C07D 333/58 (2006.01) C07D 409/12 (2006.01) C07D 413/12 (2006.01) C07D 207/06 (2006.01)
Patent
CA 2157236
The present invention provides a novel process for preparing novel compounds of formula I Image I wherein R1 and R2 each are independently C1-C4 alkyl, or combine to form piperidinyl, pyrrolidinyl, methylpyrrolidinyl, dimethylpyrrolidinyl, morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; and n is 2 or 3; or a pharmaceutically acceptable salt thereof, comprising a) reacting a haloalkyl amine of formula III Image III wherein X is a halogen; and R1, R2, and n are as defined above, with a compound of formula IV Image IV wherein R is C1-C6 alkyl, in the presence of an alkyl acetate solvent and a base; b) extracting the reaction product of step a) with an aqueous acid; and c) cleaving the ester of the reaction product from step b) to form an acid. The present invention further provides a novel process for preparing compounds of formula V Image II wherein R1 and R2 each are independently C1-C4 alkyl, or combine to form piperidinyl, pyrrolidino, methylpyrrolidino, dimethylpyrrolidinyl, morpholino, dimethylamino, diethylamino, or l-hexamethyleneimino; R3 and R4 each are H or a hydroxy protecting group; and n is 2 or 3; or a pharmaceutically acceptable salt thereof, comprising a) reacting a haloalkyl amine of formula III Image III wherein X is a halogen; and R1, R2, and n are as defined above, with a compound of formula IV Image IV wherein R is C1-C6 alkyl, in the presence of an alkyl acetate solvent and a base; b) extracting the reaction product from step a) with an aqueous acid; c) cleaving the ester of the reaction product from step b) to form an acid; d) reacting the extracted product from step c) with a compound of formula V Image V wherein R3 and R4 are as defined above, or a pharmaceutically acceptable salt thereof; e) optionally removing the R3 and R4 hydroxy protecting groups of the reaction product form step d); and f) optionally forming a salt of the reaction product from either steps d) or step e).
Kjell Douglas Patton
Perry Fred Mason
Eli Lilly And Company
Gowling Lafleur Henderson Llp
LandOfFree
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