3,4-Diaminobenzophenone → 5-Benzoyl-2-(3,5-dimethylpyrrol-2-yl)-benzimidazole

HRID 553245Notes

Reaction equation

HRID 553245 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8](O)=O.[NH2:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=1[NH2:26])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>N1C=CC=CC=1>[C:15]([C:14]1[CH:23]=[CH:24][C:25]2[N:26]=[C:8]([C:3]3[NH:4][C:5]([CH3:7])=[CH:6][C:2]=3[CH3:1])[NH:11][C:12]=2[CH:13]=1)(=[O:16])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 1355203,4-DiaminobenzophenoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27764683,5-dimethyl-1H-pyrrole-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 579557765-Benzoyl-2-(3,5-dimethylpyrrol-2-yl)-benzimidazoleYield 15.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

3,5-Dimethylpyrrole-2-carboxylic acid (99 mg, 0.71 mmol) was added to a pyridine (3 ml) solution of 3,4-diaminobenzophenone (150 mg, 0.71 mmol). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (149 mg, 0.78 mmol) and 1-hydroxybenzotriazole monohydrate (119 mg, 0.78 mmol) were further added, and the mixture was heated to 70° C. and stirred overnight. The reaction mixture was allowed to cool to room temperature with stirring, and then the solvent was evaporated. The residue was purified using medium pressure silica gel flash column chromatography (NH silica gel, chloroform:methanol=98:2). The residue was dissolved in acetic acid (3 ml), and stirred for 8 hours at 100° C. The reaction mixture was allowed to cool to room temperature with stirring, and then the solvent was evaporated. The residue was purified using medium pressure silica gel flash column chromatography (NH silica gel, chloroform:methanol=98:2), to afford 5-benzoyl-2-(3,5-dimethylpyrrol-2-yl)-benzimidazole (34 mg, 15% in two steps) as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. stirringwith stirring
  3. customthe solvent was evaporated
  4. customThe residue was purified
  5. dissolutionThe residue was dissolved in acetic acid (3 ml)
  6. stirringstirred for 8 hours at 100° C
  7. temperatureto cool to room temperature
  8. stirringwith stirring
  9. customthe solvent was evaporated
  10. customThe residue was purified

Sources & evidence

ORD record
ord-bf8b3939a272405e8ba838ce5910251d
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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