1130155-48-4

Basic information

• Product Name: (E)-4-(diMethylaMino)but-2-enoic acid (Hydrochloride)
• Synonyms: (2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride (1:?);(E)-4-(DiMethylaMino)but-2-enoic acid xhydrochloride;-4-(Dimethylamino);but-2-enoic acid xhydrochloride
• CAS NO: 1130155-48-4
• Molecular Formula: C6H12ClNO2
• Molecular Weight: 165.61798
• Mol File: 1130155-48-4.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (E)-4-(diMethylaMino)but-2-enoic acid (Hydrochloride)(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(diMethylaMino)but-2-enoic acid (Hydrochloride)(1130155-48-4)
• EPA Substance Registry System: (E)-4-(diMethylaMino)but-2-enoic acid (Hydrochloride)(1130155-48-4)

Safety Data

• Hazardous Substances Data: 1130155-48-4(Hazardous Substances Data)

Usage

Uses

4-?(Dimethylamino)?-?2-butenoic Acid Hydrochloride was used in the preparation of tricyclic nitrogen heterocyclic compounds and related heteroanalogs for the prevention or treatment of cancer.

Upstream product

• 13991-36-1 4-bromocrotonic acid 
• 124-40-3 dimethyl amine 
• 98552-51-3 ethyl 4-(dimethylamino)crotonate 
• 1259519-60-2 4-dimethylaminocrotonic acid methyl ester hydrochloride 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 1255078-56-8 (E)-ethyl 4-(dimethylamino)but-2-enoate hydrochloride 
• 212776-19-7 (E)-4-(dimethylamino)-2-butenoic acid methyl ester 
• 1413945-87-5 dimethylaminoacetaldehyde-hydrogen sulphite adduct 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 1421354-12-2 (E)-4-dimethylamino-but-2-enoic acid tert-butyl ester 

Downstream Products

• 1612182-63-4 (2E)-N-{3-[2-amino-6-(methylamino)pyrimidin-4-yl]phenyl}-4-(dimethylamino)but-2-enamide 
• 1202755-89-2 (E)-4-(dimethylamino)-N-(3-(5-fluoro-4-(m-tolylamino)pyrimidin-2-ylamino)phenyl)but-2-enamide 

Relevant articles and documents

A EGFR molecule targeting anti-tumor pharmaceutical preparation method

The invention relates to a preparation method for an EGFR molecule targeting antitumor drug, and provides a preparation method for (E)-N-[4-(3-acetylene phenyl)amino-3-cyan-7-ethoxy-6-quinolyl]-4-(dimethyl amino)-2-butylene amide. The preparation method comprises the following steps: N-(4-chloro-3-cyan-7-ethoxy quinoline-6-yl) acetamide (a compound II) and 3-aminophenylacetylene (a compound III) are subjected to a substitution reaction, and a compound IV is obtained; under an acidic or alkaline condition, the compound IV is subjected to a hydrolysis reaction, and 3-cyan-6-amino-7-ethoxy-4-(3-acetenyl anilino) quinoline (a compound V) is obtained; after trans-4-dimethylaminocrotonic acid hydrochloride (a compound VI) and an acylation reaction reagent is subjected to an acylation reaction, the product and 3-cyan-6-amino-7-ethoxy-4-(3-acetenyl anilino) quinoline (the compound V) are subjected to condensation reaction, and the finished product is obtained. The method is advantageous in that raw materials are easily available, the technology is concise, the production cost is low, and the method is economical and environmentally friendly and is suitable for industrial production.

Synthetic method for (2Z)-4-(dimethylamino)but-2-enoic acid hydrochloride

The invention discloses a synthetic method for (2Z)-4-(dimethylamino)but-2-enoic acid hydrochloride. The synthetic method comprises the following steps: under an inert gas atmosphere, dissolving [bi(2,2,2-trifluoroethoxy)-phosphinyl]methyl acetate in organic solvent, adding lithium reagent, adding alkali solution, controlling the temperature to 0-30 DEG C, adding 2-(dimethylamino)acetaldehyde sulfite, and carrying out stirring reaction, carrying out acidification, extraction and column purification after reaction to obtain the (2Z)-4-(dimethylamino)but-2-enoic acid hydrochloride. The syntheticmethod has the advantages of convenience in operation and high yield, and industrial production can be realized.

Design, synthesis and biological evaluation of WZ4002 analogues as EGFR inhibitors

A series of thirty two anilinopyrimidines derived from WZ4002 has been synthesized and evaluated for percentage inhibition of six different EGFR kinases using LanthaScreen binding assay method (EGFR d746 – 750) or Z'LYTE assay method (EGFR-WT, EGFR d746 – 750, EGFR T790M, EGFR T790M L858R, EGFR C797S and EGFR T790M L858R C797S). Ortho-hydroxyacetamide 10 exhibited complete inhibition of all the six kinases at 10 μM. Against the triple mutant, EGFR T790M C797S L858R, compounds 9–12 exhibited complete inhibition at 10 μM and nearly complete inhibition at 1 μM. The target compounds were also evaluated using the MTT assay to determine their cytotoxic activity against human non-small cell lung cancer cells (PC9, PC9GR and H460) and mouse leukemic cells (Ba/F3 WT and Ba/F3T 3151). Overall, 7, 9–12, 30 and 31 were found to be the most potent compounds across all five cell lines.