5-[Bis(2-chloroethyl)aMino]-1-Methyl-1H-benziMidazole-2-butanoic Acid Methyl Ester

Base Information

• Chemical Name: 5-[Bis(2-chloroethyl)aMino]-1-Methyl-1H-benziMidazole-2-butanoic Acid Methyl Ester
• CAS No.: 109882-25-9
• Molecular Formula: C17H23Cl2N3O2
• Molecular Weight: 372.295
• Mol file: 109882-25-9.mol

Synonyms:5-[Bis(2-chloroethyl)aMino]-1-Methyl-1H-benziMidazole-2-butanoic Acid Methyl Ester

Chemical Property of 5-[Bis(2-chloroethyl)aMino]-1-Methyl-1H-benziMidazole-2-butanoic Acid Methyl Ester

Chemical Property:

• Melting Point: 60-63 °C (decomp)
• Boiling Point: 536.4±50.0 °C(Predicted)
• PKA: 7.08±0.10(Predicted)
• PSA: 47.36000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 3.35300

Purity/Quality:

99% ^*data from raw suppliers

5-[Bis(2-chloroethyl)amino]-1-methyl-1H-benzimidazole-2-butanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Impurity of Bendamustine (B132500), an anticancer drug.

Technology Process of 5-[Bis(2-chloroethyl)aMino]-1-Methyl-1H-benziMidazole-2-butanoic Acid Methyl Ester

There total 12 articles about 5-[Bis(2-chloroethyl)aMino]-1-Methyl-1H-benziMidazole-2-butanoic Acid Methyl Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)butyric acid methyl ester hydrochloride (1221157-11-4) + chloroacetic acid (79-11-8) → 4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid methyl ester (109882-25-9)

Guidance literature:

4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)butyric acid methyl ester hydrochloride; chloroacetic acid; In tetrahydrofuran; Inert atmosphere; Heating;

With borane-THF; In tetrahydrofuran; at 20 ℃;

With methanol; In tetrahydrofuran; at 20 ℃;

Reference yield: 94.0%

methanol (67-56-1) + bendamustine hydrochloride (3543-75-7,97832-05-8) → 4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid methyl ester (109882-25-9)

Guidance literature:

With methanesulfonic acid; at 65 ℃; for 1h; Inert atmosphere;

Reference yield:

4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)butyric acid methyl ester + chloroacetic acid (79-11-8) → 4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid methyl ester (109882-25-9)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 - 58 ℃; for 2.66667h; Inert atmosphere;

upstream raw materials:

diazomethane

bendamustine

bendamustine hydrochloride

4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)butyric acid methyl ester hydrochloride

Downstream raw materials:

bendamustine hydrochloride

Refernces

• 1、 -. "BENDAMUSTINE DERIVATIVES AND METHODS OF USING SAME". Page/Page column 15. . Retrieved 2014/05/24.
• 2、 Chen, Jian,Przyuski, Katrin,Roemmele, Renee,Bakale, Roger P.. "Discovery of a novel, efficient, and scalable route to bendamustine hydrochloride: The API in Treanda". experimental part. p. 1063 - 1072. Retrieved 2012/01/04.