179688-27-8

Basic information

• Product Name: Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate
• Synonyms: 2-Amino-4,5-bis(2-methoxyethoxy)benzoic acid ester;2-Amino-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester;4,5-Bis(2-methoxyethoxy)anthranilic acid ethyl ester;Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate;Methyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate;Ethyl 2-aMino-4,5-bis(2-Methoxyethoxy)benzoate;Erlotinib interMidiate IV;Benzoic acid,2-aMino-4,5-bis(2-Methoxyethoxy)-, ethyl ester
• CAS NO: 179688-27-8
• Molecular Formula: C15H23NO6
• Molecular Weight: 313.35
• EINECS: 1592732-453-0
• Product Categories: intermidiate of Erlotinib hydrochloride;Erlotinib INTERMEDIATES
• Mol File: 179688-27-8.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 456.4 °C at 760 mmHg
• Flash Point: 183.9 °C
• Appearance: /
• Density: 1.148
• Vapor Pressure: 1.62E-08mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.52±0.10(Predicted)
• CAS DataBase Reference: Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate(179688-27-8)
• EPA Substance Registry System: Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate(179688-27-8)

Safety Data

• Hazardous Substances Data: 179688-27-8(Hazardous Substances Data)

Usage

Description

Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate, also known as 2-Amino-4,5-bis(2-methoxyethoxy)benzoic Acid Ethyl Ester, is an organic compound that serves as an intermediate in the synthesis of Erlotinib, a selective epidermal growth factor receptor (EGFR)-tyrosine kinase inhibitor and antineoplastic agent.

Uses

Used in Pharmaceutical Industry:
Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate is used as an intermediate in the synthesis of Erlotinib for its role as a selective EGFR-tyrosine kinase inhibitor and antineoplastic agent. This makes it a crucial component in the development of cancer treatments, particularly for solid tumors.

InChI:InChI=1/C15H23NO6/c1-4-20-15(17)11-9-13(21-7-5-18-2)14(10-12(11)16)22-8-6-19-3/h9-10H,4-8,16H2,1-3H3

Upstream product

• 819813-71-3 3,4-bis(2-methoxyethoxy)-benzoic acid 
• 183322-16-9 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester 
• 3943-89-3 Ethyl protocatechuate 
• 179688-26-7 2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester 

Downstream Products

• 183322-18-1 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline 
• 183319-69-9 erlotinib hydrochloride 
• 214471-57-5 N'-[2-carbethoxy-4,5-bis(2-methoxyethoxy)phenyl]-N,N-dimethylformamidine 
• 179688-29-0 6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one 
• 773071-69-5 2-(3-chloromethylbenzoylamino)-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester 
• 179688-29-0 6,7-bis-(2-methoxyethoxy)-4(3H)quinazolinone 
• 214484-83-0 4-[(3-dimethylaminophenyl)amino]-5,6-bis(2-methoxyethoxy)-3-quinolinecarbonitrile 
• 1447828-82-1 N¹-(6,7-bis(2-methoxyethoxy)quinazolin-4-yl)-N³,N³-bis(2-chloroethyl)benzene-1,3-diamine hydrochloride 
• 1456621-40-1 N¹-(6,7-bis(2-methoxyethoxy)quinazolin-4-yl)-N²,N²-bis(2-chloroethyl)benzene-1,2-diamine hydrochloride 
• 1351124-92-9 2-hydroxy-4,5-bis(2-methoxy-ethoxy)benzoic acid 
• 1351125-34-2 C₂₇H₂₈FN₃O₆ 
• 1351125-31-9 C₂₅H₂₇ClN₂O₇ 
• 1351125-29-5 C₂₆H₂₇ClFNO₇ 

Relevant articles and documents

Synthetic method of erlotinib

The invention relates to a synthetic method of erlotinib, and belongs to the technical field of chemical synthesis. The preparation method comprises the following synthesis steps: (1) reacting a compound I with 2-chloroethyl methyl ether to generate a compound II; (2) oxidizing the compound II through peracetic acid to generate a compound III; (3) reacting the compound III with benzene sulfonyl chloride to generate a compound IV; (4) carrying out a ring closing reaction on the compound IV, ammonium chloride and formamide to generate a compound V; (5) reacting the compound V with phosphorus oxychloride to generate a compound VI; and (6) reacting the compound VI with m-aminophenylacetylene to generate a compound VII erlotinib. The invention provides a new synthetic route, and the used raw materials are common materials, are simple and easily available, can adapt to production of various scales, and the synthetic method has good industrial production prospects.

Synthesis and evaluation of novel 18F-labeled quinazoline derivatives with low lipophilicity for tumor PET imaging

Four novel 18F-labeled quinazoline derivatives with low lipophilicity, [18F]4-(2-fluoroethoxy)-6,7-dimethoxyquinazoline ([18F]I), [18F]4-(3-((4-(2-fluoroethoxy)-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine ([18F]II), [18F]4-(2-fluoroethoxy)-7-methoxy-6-(2-methoxyethoxy)quinazoline ([18F]III), and [18F]4-(2-fluoroethoxy)-6,7-bis(2-methoxyethoxy)quinazoline ([18F]IV), were synthesized via a 2-step radiosynthesis procedure with an overall radiochemical yield of 10% to 38% (without decay correction) and radiochemical purities of >98%. The lipophilicity and stability of labeled compounds were tested in vitro. The log P values of the 4 radiotracers ranged from 0.52 to 1.07. We then performed ELISA to measure their affinities to EGFR-TK; ELISA assay results indicated that each inhibitor was specifically bounded to EGFR-TK in a dose-dependent manner. The EGFR-TK autophosphorylation IC50 values of [18F]I, [18F]II, [18F]III, and [18F]IV were 7.732, 0.4698, 0.1174, and 0.1176?μM, respectively. All labeled compounds were evaluated via cellular uptake and blocking studies in HepG2 cell lines in vitro. Cellular uptake and blocking experiment results indicated that [18F]I and [18F]III had excellent cellular uptake at 120-minute postinjection in HepG2 carcinoma cells (51.80?±?3.42%ID/mg protein and 27.31?±?1.94%ID/mg protein, respectively). Additionally, biodistribution experiments in S180 tumor-bearing mice in vivo indicated that [18F]I had a very fast clearance in blood and a relatively high uptake ratio of tumor to blood (4.76) and tumor to muscle (1.82) at 60-minute postinjection. [18F]III had a quick clearance in plasma, and its highest uptake ratio of tumor to muscle was 2.55 at 15-minute postinjection. These experimental results and experiences were valuable for the further exploration of novel radiotracers of quinazoline derivatives.

Preparation method of erlotinib intermediate

The invention belongs to the field of chemical synthesis and relates to a preparation method of an erlotinib intermediate 6,7-di(methoxyethoxy)quinazoline-4-one. According to the invention, by screening reaction conditions, a preparation technology of the