148901-68-2

148901-68-2 - Names and Identifiers

Name	(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenal
Synonyms	PT-4 3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl-2-propenal (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-Quinolinyl-2-propenal (E)-3-[2-Cyclopropyl-4-(4-Fluorophenyl)-3-Quinolinyl-2-Propenal (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenal (2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quin-olinyl]-2-propenal (E)-3-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)acrylaldehyde (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-en-1-al (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenal (E)-3'-[4-(4'-FLUOROPHENYL)-2-(CYCLOPROPYL)-3-QUINOLINYL]-2-PROPENAL 2-Propenal, 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-, (2E)- (E)-3''-[4-(4''-FLUOROPHENYL)-2-(CYCLOPROPYL)-3-QUINOLINYL]-2-PROPENAL
CAS	148901-68-2
InChI	InChI=1/C21H16FNO/c22-16-11-9-14(10-12-16)20-17-4-1-2-6-19(17)23-21(15-7-8-15)18(20)5-3-13-24/h1-6,9-13,15H,7-8H2/b5-3+

148901-68-2 - Physico-chemical Properties

Molecular Formula	C21H16FNO
Molar Mass	317.36
Density	1.256±0.06 g/cm3(Predicted)
Melting Point	136-142 °C
Boling Point	491.8±45.0 °C(Predicted)
Flash Point	251.228°C
Vapor Presure	0mmHg at 25°C
pKa	3.82±0.50(Predicted)
Storage Condition	2-8℃
Refractive Index	1.675

148901-68-2 - Reference Information

Introduction

(E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline-2-acrolein is pitavastatin calcium synthesis intermediate, pitavastatin calcium (PitavastatinCalcium) trade name is Livalo, it is the third-generation statin lipid-lowering drug jointly developed and produced by Japan's Nissan Chemical Industry Co., Ltd. Hexinghe Co., Ltd. This product has been listed in Japan in October 2003. It is used to treat primary hypercholesterolemia and familial hypercholesterolemia. It has good safety and effectiveness.

Preparation

(E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolin-2-acrolein is prepared as follows: 1) Add 26g 2-cyclopropyl -4-(4-fluorophenyl) quinoline -3-formaldehyde, 37.3g (triphenyl n-phosphorus) methyl acetate and 300mLDMF into a 500mL reaction bottle respectively, stir, raise the temperature to 80 ℃ for reaction, and TLC monitors the reaction; After the reaction is completed, cool to room temperature, add 800mL of water, stir to separate the liquid, the water layer is extracted with ethyl acetate (300mL × 3), and the organic phase is combined, the organic phase was washed with 500mL of water and 500mL of saturated sodium chloride solution, anhydrous sodium sulfate was dried, the solvent was evaporated under reduced pressure to obtain 63.2g of brown-yellow solid residue, 300mL of methanol was added, heated and dissolved, cooled, stirred, crystallized, filtered, rinsed, dried, and other 26.9g of light yellow solid product intermediate 1. Yield: 83%. 2) At room temperature, 25g of intermediate 1 and 5.9g of lithium bromide are placed in 230mL tetrahydrofuran, stirred for 30 minutes, 2.6g of sodium borohydride is added, then the reaction is carried out at room temperature, and TLC monitors the reaction; After the reaction of the raw materials is complete, the solvent is evaporated under reduced pressure, 100mL of water is added, and then extracted with ethyl acetate (100mL × 3); The organic layer is dried with anhydrous sodium sulfate, leached, evaporated to dry the solvent under reduced pressure, 60mL of ether, 20.5g white solid product intermediate 2. Yield: 93%. 3) In 150mL of dichloromethane, 20g of intermediate 2 is added, stirred and dissolved, then 1g of catalyst TEMPO is added, then 10mL of potassium bromide aqueous solution is added dropwise, the temperature is reduced to 0 ℃, and then 50g of 10% sodium hypochlorite solution is added dropwise. After dropping, the temperature is raised to room temperature for reaction, and TLC is used to detect the reaction. After the reaction is completed, 50mL of water is added into the reaction solution, stirred, left to layer, and the water layer is extracted; the organic phase was combined, washed with 50mL of saturated sodium sulfite solution and 50mL of saturated salt water, dried with anhydrous sodium sulfate, and concentrated to dry under reduced pressure to obtain 16.9g of product (E)-3-[2-cyclopropyl -4-(4-fluorophenyl)-3-quinoline -2-acrolein. The yield was 85%.

Last Update：2024-04-09 21:04:16