Patent ID: 8399660
Filing Date: 2013-03-19
Classification: A61P,C07D,C07F

Abstract:
1. A process for preparing a compound (I-b) having the formula comprising the steps of: (Step 1) combining a compound (II-b) having the formula: with a compound (III) having the formula: in a solvent, optionally in the presence of a copper catalyst, to form a compound (IV-b) having the formula: (Step 2) combining a compound (IV-b) with a compound (V) having the formula: in a solvent in the presence of a reducing agent to form compound (VI-b) having the formula (Step 2-1) combining a compound (VI-b) with a protecting group reagent in a solvent in the presence of a base to form protected compound (VI-b-P) having the formula (Step 3) combining a compound (VI-b-P) with a compound (VII) having the formula: in a solvent in the presence of a base and a palladium catalyst to form compound (VIII-b-P) having the formula: (Step 3-1) deprotecting a compound (VIII-b-P) in a solvent in the presence of an acid to form compound (VIII-b) or a salt thereof having the formula: (Step 4) heating compound (VIII-b) in a solvent in the presence of an acid, followed by the addition of a neutralizing agent to form compound (I-b) A is selected from: phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; B is selected from: phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; Het-CH Q is a borane having the formula —BY alternatively, Q is a BF X is selected from: a) —CH Z is selected from: a) I, b) Br, c) Cl, d) R R R R R R R R R R R m is 0, 1, 2, 3, or 4; n is 0, 1, 2, 3, or 4; p, at each occurrence, independently is 0, 1, or 2; s is 1, 2, 3, 4, 5, or 6; and t is 0, 1, 2, 3, 4, 5, or 6, wherein —(CH 2 ) s — and —(CH 2 ) t , other than when t is 0, are optionally substituted on any carbon atom thereof by one or more moieties selected from a) C 1-6 alkyl, b) C 1-6 alkenyl, c) phenyl, d) hydroxyl, e) C 1-6 alkoxy, f) F, g) Cl, h) Br, i) I, j) ═O, and k) benzyl.