717-94-2

Basic information

• Product Name: 3,5-DIMETHOXYPHENYLPROPIONIC ACID
• Synonyms: 3-(3,5-DIMETHOXYPHENYL)PROPIONIC ACID;3,5-DIMETHOXYPHENYLPROPIONIC ACID;3-(3,5-DIMETHOXYPHENYL)PROPANOIC ACID;3,5-DiMethoxy-benzenepropanoic acid;4-[(3R,5S)-4-[(tert-butoxy)carbonyl]-3,5-dimethylpiperazin-1-yl]benzoic acid
• CAS NO: 717-94-2
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Product Categories: Aromatic Propionic Acids;Organic acids
• Mol File: 717-94-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 60-62°C
• Boiling Point: 175°C 1mm
• Flash Point: 141.1 °C
• Appearance: /
• Density: 1.159 g/cm³
• Vapor Pressure: 6.25E-06mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4?+-.0.10(Predicted)
• CAS DataBase Reference: 3,5-DIMETHOXYPHENYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHOXYPHENYLPROPIONIC ACID(717-94-2)
• EPA Substance Registry System: 3,5-DIMETHOXYPHENYLPROPIONIC ACID(717-94-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 717-94-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

3-(3,5-Dimethoxyphenyl)propanoic acid is a derivative of 3-(3,4-Dimethoxyphenyl)propanoic Acid (D460730), which is one of the novel circulating coffee metabolites in human plasma.

InChI:InChI=1/C11H14O4/c1-14-9-5-8(3-4-11(12)13)6-10(7-9)15-2/h5-7H,3-4H2,1-2H3,(H,12,13)/p-1

Upstream product

• 22243-98-7 3-(3-hydroxy-5-methoxy-phenyl)-propionic acid 
• 77-78-1 dimethyl sulfate 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 105-53-3 diethyl malonate 
• 886-51-1 Methyl 3-(3',5'-dimethoxyphenyl)propionate 
• 16909-11-8 3-(3,5-dimethoxyphenyl)acrylic acid 
• 20767-04-8 (E)-3,5-dimethoxycinnamic acid 
• 618084-27-8 5-(3,5-dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 10272-07-8 3.5-dimethoxyaniline 
• 93092-27-4 methyl α-bromohydrocynnamate 
• 41514-66-3 5'-methoxy-3',4'-methylenedioxy cinnamic acid 
• 64-18-6 formic acid 
• 40243-87-6 3,5-dimethoxystyrene 

Downstream Products

• 1080-05-3 3-(3,5-dimethoxyphenyl)-1-propanol 
• 872267-05-5 3-(3,5-dimethoxy-phenyl)-propionic acid amide 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 4778-99-8 2-carboxymethyl-4,6-dimethoxy-benzoic acid 
• 61262-81-5 cannabispirone 
• 76842-70-1 7-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one 
• 76842-61-0 5,7-dimethoxyindan-1-carbonitrile 
• 69636-83-5 α-cannabispiranol 
• 64052-90-0 β-cannabispiranol 
• 71135-80-3 cannithrene-1 
• 91555-31-6 4-(3,5-dimethoxyphenyl)butanoic acid 
• 99050-38-1 4-(3,5-Dimethoxyphenyl)butyric acid methyl ester 
• 99050-43-8 8-Benzyloxy-6-methoxytetralone 
• 99050-39-2 6,8-Dimethoxy-2-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one 

Relevant articles and documents

Cobalt-catalyzed cross-coupling reactions of aryl- And alkylaluminum derivatives with (hetero)aryl and alkyl bromides

A simple cobalt complex, such as Co(phen)Cl2, turned out to be a highly efficient and cheap precatalyst for a host of cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl and alkyl bromides. New C(sp2)-C(sp2) and C(sp2)-C(sp3) bonds were formed in good to excellent yields and with high chemoselectivity, under mild reaction conditions.

New and convergent synthesis of AZD 4547

A practical and convergent synthetic route of AZD 4547 was developed successfully. The intermediate 5-(3,5-dimethoxyphenylethyl)-1H-pyrazol-3-amine (7) was prepared from 3,5-dimethoxybenzaldehyde through 6 simple steps in 52.3% yield. Another intermediate 4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzoic acid (14) was synthesized from ethyl 4-fluorobenzoate and (2R,6S)-2,6-dimethylpiperazine in 62% yield over 2 steps. Finally, AZD 4547 was obtained from 7 and 14 in 73% yield and 99.1% purity. Purification methods of the intermediates and the final product involved in the route were developed.

Method for preparing AZD4547, intermediate and preparation method of intermediate

The invention provides a method for preparing AZD-4547. The method comprises the following steps: (1) preparing a first intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate; (2) preparinga second intermediate 5-[2-(3, 5-dimethoxyphenyl) ethyl]-1H-pyrazole-3-amine by taking the first intermediate as a raw material; and (3) in an alkali-containing organic solvent, carrying out a reaction on a third intermediate 4-((3S, 5R)-3, 5-dimethylpiperazinyl-1-yl) benzoyl chloride and the second intermediate to prepare the AZD-4547. The method has the advantages of accessible raw materials, simple technique, mild reaction conditions, convenient operation, high yield and low cost and can easily implement industrial production. The invention also provides an intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate for preparing AZD-4547 and a preparation method thereof.