3,4-Diaminobenzophenone → HCID 67166301, compound

HRID 553251Notes

Reaction equation

HRID 553251 reaction equation
[N:1]1([C:6]2[O:10][C:9]([C:11](O)=O)=[C:8]([CH3:14])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[NH2:30])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>N1C=CC=CC=1>[N:1]1([C:6]2[O:10][C:9]([C:11]3[NH:15][C:16]4[CH:17]=[C:18]([C:19](=[O:20])[C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH:27]=[CH:28][C:29]=4[N:30]=3)=[C:8]([CH3:14])[CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 1355203,4-DiaminobenzophenoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67166220HCID 67166220, compound

Product 1

HCID 67166301HCID 67166301, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

5-Pyrrolidine-1-yl-methyl-furan-2-carboxylic acid (62% purity, 223 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 reaction mixture was heated to 70° C. and stirred overnight. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated. The residue was purified using medium pressure silica gel flash column chromatography (NH silica gel, chloroform:methanol=98:2), and the obtained residue was dissolved in acetic acid (3 ml) and stirred at 100° C. for 8 hours. The solution 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 2-(5-pyrrolidine-1-yl-methyl-furan-2-yl)-5-benzoylbenzimidazole (143 mg, 55% in two steps) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-8145ef8c58474ffab2c737721ccbeed7
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

Loading…