155405-79-1

Basic information

• Product Name: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester
• CAS NO: 155405-79-1
• Molecular Formula: C₁₂H₁₃BrO₃
• Molecular Weight: 285.133789
• Mol File: 155405-79-1.mol

Chemical Properties

• CAS DataBase Reference: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester(155405-79-1)
• EPA Substance Registry System: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester(155405-79-1)

Safety Data

• Hazardous Substances Data: 155405-79-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into complex molecular structures, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester is used as a precursor in the production of various agrochemicals, potentially enhancing crop protection and yield through its incorporation into active ingredients.
Used in Organic Chemistry Research:
4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester is utilized as a building block in organic chemistry research for the exploration of new chemical reactions and the synthesis of novel organic compounds, expanding the scope of chemical knowledge and innovation.
Used in Medicinal Chemistry:
4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester is employed as a starting material in medicinal chemistry for the design and synthesis of new pharmaceutical agents, leveraging its unique structural features to target specific biological activities and therapeutic effects.
As a Hazardous Material:

Upstream product

• 106200-41-3 4-(4-carbomethoxyphenyl)butanal 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 123910-86-1 4-(4-hydroxybut-1-ynyl)benzoic acid methyl ester 
• 123910-88-3 methyl 4-(4-hydroxybut-1-yl)benzoate 
• 619-44-3 methyl 4-iodobenzoate 
• 108-88-3 toluene 
• 4619-20-9 3-(4-methylbenzoyl)propionic acid 
• 57498-54-1 methyl 4-(4-methylphenyl)-4-oxobutanoate 

Downstream Products

• 137281-39-1 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid 
• 146943-43-3 N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 
• 165049-28-5 N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 4-methylbenzenesulfonic acid salt 
• 1209465-70-2 C₂₀H₁₉N₇O₅ 

Relevant articles and documents

Multi-arm polymeric prodrug conjugates of pemetrexed-based compounds

Among other aspects, provided herein are multi-arm polymeric prodrug conjugates of pemetrexed-based compounds. Methods of preparing such conjugates as well as methods of administering the conjugates are also provided. Upon administration to a patient, release of the pemetrexed-based compound is achieved.

Synthetic pemedolac preparation process

The invention discloses a synthetic pemedolac preparation method, which specifically comprises: carrying out a Heck reaction by using methyl p-bromobenzoate and 3-butene-1-ol as starting raw materialsto obtain crude aldehyde, and directly carrying out a bromination reaction, a cyclization reaction and a hydrolysis reaction through a one-pot method to obtain pemedolac. According to the present invention, the method has characteristics of mild reaction conditions, easy control, simple and safe process operation, good product yield and high product purity.

Synthesis and antiviral study of novel 4-(2-(6-amino-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyrimidin-3-yl)ethyl)benzamide derivatives

A series of ten new compounds (7a–j) has been synthesized by absolutely replacing the glutamic acid part of Pemetrexed drug, chemically known as N-{4-[2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-l-glutamic acid, with primary, secondary, and aryl amines in high yields using diethylphosphorocyanidate (DEPC) as a peptide coupling agent. All the synthesized compounds are characterized by 1H and 13C NMR, LCMS, and FT-IR spectral techniques. All the synthesized novel non-glutamate 4-(2-(6-amino-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyrimidin-3-yl)ethyl)benzamide derivatives showed 4- to 7-folds higher antiviral activity than its structurally similar commercial drug Pemetrexed against Newcastle disease virus, an avian paramyxovirus. Among the lot, compounds possessing carboxamide synthesized using five-membered heteroaryl amines (7i and 7j) exhibited the highest antiviral activity. [Figure not available: see fulltext.].

Method for preparing pemetrexed disodium key intermediate

The invention discloses a method for preparing a pemetrexed disodium key intermediate (I). The method comprises the following steps: carrying out classical Friedenylation and esterification reactionson raw materials comprising toluene and succinic anhydride to obtain methyl 3-(4-methylphenyl)-4-oxobutanoate, carrying out oxygen or air oxidation on the methyl 3-(4-methylphenyl)-4-oxobutanoate under the catalysis of N-hydroxyphthalimide (NHPI) and cobalt acetate to obtain 4-(methoxy-4-oxobutylcarbonyl)benzoic acid, and carrying out selective reduction, selective oxidation, esterification and bromination reactions on the obtained oxidation product to prepare methyl 4-(3-bromo-4-oxobutyl)benzoate. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, simplicity in treatment, good yield and good purity of the product, and suitableness for industrial production.

An Efficient Synthesis of Pemetrexed Disodium

An efficient synthetic method for the pemetrexed disodium has been developed using methyl 4-iodobenzoate and 3-buten-1-ol as starting materials via six steps. The developed process avoided some tedious workup procedures and unfriendly reagents compared with the reported synthetic routes. In addition, two impurities generated in the process were isolated and characterized by 1H NMR, 13C NMR, and HRMS. The mechanisms of the two impurities were also discussed, and the impurities could be easily removed by suitable workup procedures. The overall yield of pemetrexed disodium was increased from 12.8% (literature) to 34.9%. Therefore, this cost-effective, environmental friendly, and high-yielding process is more suitable for scale-up production of pemetrexed disodium.

PROCESS FOR THE PREPARATION OF PEMETREXED AND LYSIN SALT THEREOF

The present invention refers to a process for the synthesis of pemetrexed and salts thereof, in particular to a lysine salt thereof, to said salt as such and to pharmaceutical compositions that comprise the same. Furthermore, the present disclosure also relates to a crystalline form of the synthesis intermediate pemetrexed diethyl ether and a crystalline form of the pemetrexed lysine salt.

PROCESSES FOR PREPARING PEMETREXED DISODIUM AND ITS INTERMEDIATE,4-(4-CARBOMETHOXYPHENYL)BUTANAL

The present invention provides a process for preparing pemetrexed disodium and its intermediate, 4-(4-carbomethoxyphenyl)butanal. The process for preparing the intermediate comprises the following steps: condensing methyl 4-bromobenzoate with 3-buten-1-ol; extracting with an organic solvent during the work-up; adding silica gel to decolorize; and evaporating the organic solvent to give 4-(4-carbomethoxyphenyl)butanal. The product obtained by the present process, with a yield of higher than 80%, and a purity measured by GC of higher than 95%, may be directly used in the next bromination reaction for synthesizing pemetrexed disodium without purification. The present process is suitable for industrial production, as the operation is simple and the reagents used are cheap and readily available.

Determination of the source of the N-methyl impurity in the synthesis of pemetrexed disodium heptahydrate

The synthesis of Pemetrexed Disodium Heptahydrate has consistently resulted in a very low level (ca. 0.02%) unknown impurity. To ensure long-term control, the identity and source of the impurity were desired. Isolation and characterization identified the impurity as the N-methyl derivative. The source was identified as the methyl groups on the peptide coupling agent, 2,6-Dimethoxy-1,3,5-triazine (CDMT). Further work assured the current conditions provide adequate control.

A practical synthesis of multitargeted antifolate LY231514

A concise and scalable synthesis of LY231514 (1), a new pyrrolo[2,3-d]pyrimidine-based antitumor agent, is presented. Reaction of 2-bromo-4-arylbutanal 9 with 2,4-diamino-6-hydroxypyrimidinc (10) regioselectively provided pyrrolo[2,3-d]pyrimidine 11, representing the core structure of the drug, in good yield. Assimilation of the glutamic acid residue by conventional means completed the synthesis. Development of the optimized synthetic route emphasized avoiding isolation of the relatively unstable aldehyde and bromoaldehyde intermediates.

Process for preparing 5-substituted pyrrolo-[2,3-d]pyrimidines

Processes for preparing 5-substituted pyrrolo[2,3-d]pyrimidines which are useful as intermediates for the preparation of pyrrolo[2,3-d]pyrimidine antineoplastic agents or as antineoplastic agents themselves are provided.