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US 11,542,244 B2Granted
Synthesis of tipifarnib
AssigneeKura Oncology, Inc.
InventorsPingda Ren, Xiaohu Deng, Wanping Mai
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Abstract
Provided herein are methods of preparing a desired enantiomer 6-[amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl) methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone, otherwise known as tipifarnib.
Claims29
A method for preparing a desired enantiomer of tipifarnib comprising the steps of:
- (i) obtaining a starting material comprising tipifarnib that is not enantiopure in the desired enantiomer;
- (ii) transforming the starting material from step (i) to a racemic mixture of tipifarnib;
- and
- (iii) recovering the desired enantiomer of tipifarnib from the racemic mixture of tipifarnib of step (ii);
- wherein step (ii) comprises the steps of:
- (ii)(a) reacting the starting material with sodium nitrite in a reaction solvent to give a product mixture;
- (ii)(b) recovering a racemic alcohol of Formula (II) from the product mixture of step (ii)(a);
- and
- (ii)(c) transforming the racemic alcohol of step (ii)(b) to the racemic mixture of tipifarnib.
6 more elements
A method for preparing a desired enantiomer of tipifarnib comprising the steps of:
- (i) obtaining a starting material comprising tipifarnib that is not enantiopure in the desired enantiomer;
- (ii) transforming the starting material from step (i) to a racemic mixture of tipifarnib;
- and
- (iii) recovering the desired enantiomer of tipifarnib from the racemic mixture of tipifarnib of step (ii),
- wherein step (ii) comprises the steps of:
- (ii)(a) heating the starting material in a reaction solvent to give a product mixture;
- (ii)(b) recovering a racemic alcohol of Formula (II) from the product mixture of step (ii)(a);
- and
- (ii)(c) transforming the racemic alcohol of step (ii)(b) to the racemic mixture of tipifarnib.
6 more elements
Dependencies are inferred from the claim text.