ChemicalBook CAS DataBase List Neratinib

Neratinib synthesis

9synthesis methods

Product Name:Neratinib
CAS Number:698387-09-6
Molecular formula:C30H29ClN6O3
Molecular Weight:557.04

52334-92-6
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Phosphonic acid, P-[2-[[4-[[3-chloro-4-(2-pyridinylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]amino]-2-oxoethyl]-, diethyl ester

1269662-79-4
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698387-09-6
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Yield:698387-09-6 95.9%

Reaction Conditions:

Stage #1: diethyl ({[4-({3-chloro-4-[(pyridin-2-yl)methoxy]phenyl}amino)-3-cyano-7-ethoxyquinolin-6-yl]carbamoyl}methyl)phosphonatewith sodium ethanolate;lithium chloride in ethanol at -5; for 0.5 h;
Stage #2: 2-(N,N-dimethylamino)ethoxide in ethanol; for 0.666667 h;Temperature;Solvent;Reagent/catalyst;

Steps:

7 Synthesis of Nearatinib

To 150mL Anhydrous ethanol in turn added to a solution of N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-2-diethylphosphate-acetamide in (12.5 g, 0.02 mol)Lithium chloride 4.2 g (0.1 mol)Down to -5 ° C,Adding sodium ethoxide 4. 1g (0.06 mil)Stirring 0.5h,Dropping 0.06 mol of dimethylaminoacetaldehyde diethyl acetal prepared by liquid A,Drip continued to respond 40min.500 mL of ethyl acetate was added,Filtered and the filtrate was added to 500 mL of water.The organic layer was separated and washed with 2 X 200 mL of ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate. Concentrated to dryness under reduced pressure and recrystallized from acetonitrile / THF to give 10.7 g of a pale yellow powder, Yield 95.9%.

References:

CN103588755,2016,B Location in patent:Paragraph 0038; 0039

848139-78-6 Synthesis