Benzimidazol-2-one → HCID 131722463, compound

HRID 1533173Notes

Reaction equation

HRID 1533173 reaction equation
N1[C:2](=[O:10])N=C2C=CC=CC=12.[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=1[NH2:23])(=[O:13])[CH3:12]>C(#N)C>[C:21]([C:18]1[CH:19]=[CH:20][C:15]2[N:14]([C:11](=[O:13])[CH3:12])[C:2](=[O:10])[NH:23][C:16]=2[CH:17]=1)#[N:22]

Participants

4

Reactant 2

HCID 162542Benzimidazol-2-oneHCID 18545772HCID 18545772, compound

Product 1

HCID 131722463HCID 131722463, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
77 °C

Procedure

6—Cyano-3N-acetylbenzimidazolone (1.47 mmol, 0.29 g) which was synthesized similarly to its benzimidazolone analog except that 1N-acetyl-2-amino-4-cyanoaniline was used as starting material and 3-(4-biphenyl)-1,2-propen-3-one (1.37 mmol, 0.29 g) were combined in 15 mL of acetonitrile to form a suspension. The reaction mixture was warmed to 77° C. and heated for 24 h. The reaction mixture was concentrated and the resulting residue was purified by standard chromatographic technique to give crude 1-(4-biphenylcarbonyl)ethyl-6-cyano- 3N-acetylbenzimidazolinone. The crude material was subjected to Pinner conditions followed by reaction with ammonium carbonate to give the title compound 1-(4- biphenylcarbonyl)ethyl-6-amidinobenzimidazolinone. LRMS: m/z 385 (M+H,100). HRMS: calcd for C23H21N4O2, 385.166451; found, 385.167149.

Workup

  1. customto form a suspension
  2. temperatureheated for 24 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting residue was purified by standard chromatographic technique
  5. customto give crude 1-(4-biphenylcarbonyl)ethyl-6-cyano- 3N-acetylbenzimidazolinone

Sources & evidence

ORD record
ord-1f9382cb36da42819fe412c08dfad68e
Source dataset
uspto-grants-2001_03
Patent number
US06207697B1

Reaction notes

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