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 207/06 (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)
Patent
CA 2157235
The present invention provides a novel process for preparing a compound of formula I Image wherein R is C1-C4 alkyl; R1 and R2 each are independently C1-C4 alkyl, or combine to form piperidinyl, pyrrolidinyl, methylpyrrolidino, dimethylpyrrolidino, morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; and n is 2 or 3; or a pharmaceutically acceptable salt thereof, comprising a) condensing (C1-C4 alkyl) 4-hydroxybenzoate with ethylene carbonate or propylene carbonate in the presence of a condensation catalyst and a moderately polar, water immiscible solvent having a high boiling point; b) reacting the product of step a), a compound of formula III Image III wherein R and n are as defined above, with a leaving group donor; and c) reacting the product of step b), a compound of formula IV Image IV wherein R and n are as defined above and X is a leaving group, with a base selected from the group consisting of piperidine, pyrrolidine, methylpyrrolidine, dimethylpyrrolidine, morpholine, dimethylamine, diethylamine, and 1-hexamethyleneimine. The product of the above process, a compound of formula I, also is novel and is useful for the preparation of pharmaceutically active compounds of formula II, particularly via the following novel process Image wherein R is C1-C4 alkyl; R1 and R2 each are independently C1-C4 alkyl, or combine to form piperidinyl, pyrrolidinyl, methylpyrrolidino, dimethylpyrrolidino, morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; and n is 2 or 3; or a pharmaceutically acceptable salt thereof, comprising a) condensing (C1-C4 alkyl) 4-hydroxybenzoate with ethylene carbonate or propylene carbonate in the presence of a condensation catalyst and a moderately polar, water immiscible solvent having a high boiling point; b) reacting the product of step a), a compound of formula III Image III wherein R and n are as defined above, with a leaving group donor; c) reacting the product of step b), a compound of formula IV Image IV wherein R and n are as defined above; and X is a leaving group, with a base selected from the group consisting of piperidine, pyrrolidine, methylpyrrolidine, dimethylpyrrolidine, morpholine, dimethylamine, diethylamine, and 1-hexamethyleneimine; d) reacting the product of step c) with a compound of formula IV Image wherein R3 and R4 are as defined above, or a pharmaceutically acceptable salt thereof; e) optionally removing the reaction product from step d); and f) optionally forming a salt of the reaction product from either step d) or step e).
Eli Lilly And Company
Gowling Lafleur Henderson Llp
LandOfFree
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