Synthesis of piperazines, piperidines and related compounds
AssigneeLexicon Pharmaceuticals, Inc.
InventorsHugh Alfred Burgoon, Ramanaiah C. Kanamarlapudi, Wenxue Wu
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Abstract
Novel methods of synthesizing piperazines, piperidines and related compounds are disclosed, as are compounds useful for their preparation.
Claims33
A method of preparing a compound of formula I:
- or a salt or solvate thereof, which comprises contacting a compound of formula IV with a compound of formula V:
- under conditions sufficient for the formation of the compound of formula I, wherein:
- Y-Z is C(O), O, CHOH or CH2;
- A is N or CH;
- G is CH or N;
- each E is independently N or CH;
- each R1 is independently fluorine, chlorine or optionally substituted alkyl, aryl, or aralkyl;
- R2 is H or ═O;
- each R3 is independently H, fluorine, chlorine or optionally substituted alkyl, aryl, aralkyl, heterocycle, or heterocycloalkyl;
- m is 1, 2 or 3;
- n is 1 or 2;
- p is 1 or 2;
- and
- q is 1-3.
A method of preparing (3′-chloro-biphenyl-4-yl)-(1-pyrimidin-2-yl-piperidin-4-yl)-methanone, or a salt or solvate thereof, which comprises contacting (3′-chloro-biphenyl-4-yl)-piperidine-4-yl-methanone with 2-chloropyrimidine under conditions sufficient for the formation of (3′-chloro-biphenyl-4-yl)-(1-pyrimidin-2-yl-piperidin-4-yl)-methanone.
A method of preparing (3′-chloro-biphenyl-4-yl)-piperidine-4-yl-methanone or a salt thereof, which comprises contacting 3-chlorophenyl boronic acid and (4-bromophenyl)(piperidine-4-yl)methanone with a transition metal catalyst under conditions sufficient for the formation of 3′-chloro-biphenyl-4-yl)-piperidine-4-yl-methanone.
(3′-Chloro-biphenyl-4-yl)-piperidine-4-yl-methanone, or a salt or solvate thereof.
Dependencies are inferred from the claim text.