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CAS No.: | 16506-27-7 |
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Name: | Bendamustine |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C16H21Cl2N3O2 |
Molecular Weight: | 358.268 |
Synonyms: | 2-Benzimidazolebutyricacid, 5-[bis(2-chloroethyl)amino]-1-methyl- (8CI);5-(Bis(2-chloroethyl)amino)-1-methyl-2-benzimidazolebutyric acid;Treanda;w-[1-Methyl-5-[bis(b-chloroethyl)amino]-2-benzimidazolyl]butyricacid; |
Density: | 1.318 g/cm3 |
Boiling Point: | 585.166 °C at 760 mmHg |
Flash Point: | 307.697 °C |
PSA: | 58.36000 |
LogP: | 3.26460 |
bendamustine hydrochloride
bendamustine
Conditions | Yield |
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With triethylamine In methanol other reagent; | 89% |
4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester
bendamustine
Conditions | Yield |
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With thionyl chloride In dichloromethane at 5 - 20℃; for 16h; | 73% |
bendamustine
Conditions | Yield |
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With sodium hydroxide In water |
bendamustine
Conditions | Yield |
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Stage #1: 4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester With water Alkaline conditions; Stage #2: With hydrogenchloride In water pH=~ 6 - ~ 7; |
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
bendamustine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 2: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C View Scheme |
6-fluoro-3-nitroaniline
bendamustine
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: hydrogenchloride / toluene / 4 h / 85 °C 1.2: 3 h / 75 °C 2.1: sulfuric acid / 10 h / Reflux 3.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 4.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 5.1: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C View Scheme |
glutaric anhydride,
bendamustine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride / toluene / 4 h / 85 °C 1.2: 3 h / 75 °C 2.1: sulfuric acid / 10 h / Reflux 3.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 4.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 5.1: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C View Scheme |
4-(1-methyl-5-nitro-1H-benzimidazol-2-yl)butanoic acid
bendamustine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sulfuric acid / 10 h / Reflux 2: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 3: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 4: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C View Scheme |
4‐(1‐methyl‐5‐nitro‐1H‐benzoimidazol‐2‐yl)butyric acid ethyl ester
bendamustine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 2: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 3: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C View Scheme |
bendamustine
4-(5-(bis(2-chloroethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butan-1-ol
Conditions | Yield |
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Stage #1: bendamustine With borane-THF In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With water In tetrahydrofuran at 0℃; | 86% |
The 4-{5-[Bis-(2-chloro-ethyl)-amino]-1-methyl-1H-benzoimidazol-2-yl}-butyric acid, with the CAS registry number 16506-27-7, is also known as 1H-Benzimidazole-2-butanoic acid, 5-[bis (2-chloroethyl)amino]-1-methyl-, monohydrochloride. This chemical's molecular formula is C16H21Cl2N3O2 and molecular weight is 358.26. What's more, its IUPAC name is 4-[5-[Bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid and systematic name is called 4-{5-[Bis(2-chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoic acid.This chemical's classification code is Antineoplastic Agents. It is a nitrogen mustard used in the treatment of chronic lymphocytic leukemias and lymphomas. It belongs to the family of drugs called alkylating agents. It is also being studied for the treatment of sarcoma.
Physical properties about 4-{5-[Bis-(2-chloro-ethyl)-amino]-1-methyl-1H-benzoimidazol-2-yl}-butyric acid are: (1) ACD/LogP: 2.69; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): 0.81; (4) ACD/LogD (pH 7.4): 0.05; (5) ACD/BCF (pH 5.5): 1; (6) ACD/BCF (pH 7.4): 1; (7) ACD/KOC (pH 5.5): 9.11; (8) ACD/KOC (pH 7.4): 1.57; (9) #H bond acceptors: 5; (10) #H bond donors: 1; (11) #Freely Rotating Bonds: 9; (12) Polar Surface Area: 47.36 Å2; (13) Index of Refraction: 1.599; (14) Molar Refractivity: 92.87 cm3; (15) Molar Volume: 271.7 cm3; (16) Surface Tension: 47.1 dyne/cm; (17) Density: 1.31 g/cm3; (18) Flash Point: 307.7 °C; (19) Enthalpy of Vaporization: 91.95 kJ/mol; (20) Boiling Point: 585.2 °C at 760 mmHg; (21) Vapour Pressure: 1.55E-14 mmHg at 25 °C.
Preparation of 4-{5-[Bis-(2-chloro-ethyl)-amino]-1-methyl-1H-benzoimidazol-2-yl}-butyric acid: this chemical is prepared by reaction of Cytostasan.
This reaction needs reagent N(C2H5)3 and solvent Methanol. The yield is 89 %.
You can still convert the following datas into molecular structure:
(1) SMILES: ClCCN(c2ccc1c(nc(n1C)CCCC(=O)O)c2)CCCl
(2) InChI: InChI=1/C16H21Cl2N3O2/c1-20-14-6-5-12(21(9-7-17)10-8-18)11-13(14)19-15(20)3-2-4-16(22)23/h5-6,11H,2-4,7-10H2,1H3,(H,22,23)
(3) InChIKey: YTKUWDBFDASYHO-UHFFFAOYAV