Benzimidazol-2-one

Chemical Name 5-Chloro-1-[1-[3-(2,3-dihydro-2-oxo-1 H-benzimidazol-1-yl)-propyll -4-pi-peridinyl] -1,3-dihydro-2H-benzimidazol-2-one... 

A mixture of 2.3 parts of 1-(3-chloropropyl)-1 -dihydro-2H-benzimidazol-2-one, 2.5 parts of 5-chloro-1 -dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate,... 

CN l-[l-[4-(4-fluorophenyl)-4-oxobutyl]-l,2,3,6-tetrahydro-4-pyridinyl]-l,3-dihydro-2//-benzimidazol-2-one... 

Oxatomide (l- 3- [4-(diphenylmethyl)-l-piperazinyl] propyl)-l,3-dihydro-2H-benzimidazol-2-one) is an antiallergy drug. Akamatsu has reported that oxatomide decreases neutrophil-generated superoxide anion and hydrogen peroxide formation in a dose-dependent manner. The authors hypothesize that the drug is inhibiting NADPH-dependent oxygen metabolism within the neutrophil (Akamatsu et al., 1993). 

Azide 367 is prepared from 4-r -butyl-2-nitroaniline in 76% yield by its diazotization followed by treatment with sodium azide. In a 1,3-dipolar cycloaddition with cyanoacetamide, azide 367 is converted to triazole 368 that without separation is directly subjected to Dimroth rearrangement to give derivative 369 in 46% yield. Reduction of the nitro group provides ortfc-phenylenediamine 371 in 91% yield <2000EJM715>. Cyclocondensation of diamine 371 with phosgene furnishes benzimidazol-2-one 370 in 39% yield, whereas its reaction with sodium nitrite in 18% HC1 leads to benzotriazole derivative 372, which is isolated in 66% yield (Scheme 59). Products 370 and 372 exhibit potassium channel activating ability <2001FA841>. 

Molecules related to calixarenes may also form hydrogen bonded network structures. The heterocalixarene (calix[l]benzimidazol-2-one[2]arene) 17 forms... 

The marker residue for triclabendazole is 5-chloro-6-(2, 3 -dichlorophe-noxy)-benzimidazole-2-one, a compound formed when common fragments of triclabendazole-related residues are hydrolyzed under alkaline conditions at 90-100 C. Since the marker residue does not represent total residues, the marker residue levels are converted to triclabendazole equivalents using a conversion factor of 1.09 (31). 

Kawamoto, H., Ozaki, S., Itoh, Y., Miyaji, M., Arai, S., Nakashima, H., Kato, T., Ohta, H., Iwasawa, Y. Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist 1 -[(3R, 4R)-1-Cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397), J. Med. Chem. 1999, 42, 5061-5063. 

A mixture of 2.3 parts of l-(3-chloropropyl)-l,3-dihydro-2H-benzimidazol-2-one, 2.5 parts of 5-chloro-l,3-dihydro-l-(4-piperidinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 part of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours. The reaction mixture is cooled to room temperature and water is added. The undissolved product is filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and 10% methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and recrystallized from a mixture of N,N-dimethylformamide and water, yielding 1.3 parts (30%) of 5-chloro-l-[l-[3-(l,3-dihydro-2-oxo-2H-benzimidazol-l-yl)propyl]-4-piperidinyl]-l,3-dihydro-2H-benzimidazol-2-one MP 242.5°C. 

Chemical Name 2H-Benzimidazol-2-one, l,3-dihydro-l-[l-[(4-methyl-4H,6H-pyrrolo[l,2-a][4,l]benzoxazepin-4-yl)methyl]-4-piperidinyl]-, maleate (1 1)... 

D i methoxytetra hyd rof u ra n Lithium aluminum hydride Tetramethylethylene diamine l,3-Dihydro-l-(4-piperidyl)-2H-benzimidazol-2-one... 

To a solution of 7.5 g thereof, in 300 ml of tetrahydrofuran is added 5 g of l,l -carbonyldiimidazole and the resultant mixture stirred at room temperature for 1 hour. To this mixture is added 5 g of l,3-dihydro-l-(4-piperidyl)-2H-benzimidazol-2-one, and the reaction is heated at reflux temperature for 48 hours. After cooling to room temperature, the reaction mixture is poured into 150 ml of ice-water and extracted into 150 ml of methylene chloride. The organic extracts are washed successively with 150 ml of sodium carbonate solution, 150 ml of water and 150 ml of dilute hydrochloric acid, then dried over magnesium sulfate, filtered, and the solvent is evaporated under reduced pressure to yield l,3-dihydro-l- l-[(4-methyl-4H,6H-pyrrolo[l,2-a][4,l]benzoxazepin-4-yl)carbonyl]-4-piperidinyl -2H-benzimidazol-2-one, m.p. 208°-210°C. 

Sodium hydride Hydrochloric acid Aluminum chloride o-Phosphoric acid Sodium hydroxide Palladium on carbon Sodium borohydride l,3-Dihydro-l-benzyl-2H-benzimidazol-2-one... 

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