Reaction #1135836

ord-048edf16fb2344398b4f0b6ef2882102

Reaction equation

Nc1ccc(-c2ccccc2)cc1NC(=O)CCCCCCC(=O)[O-]
8-(4-aminobiphenyl-3-ylamino)-8-oxooctanoate
CC(=O)O
acetic acid
→
COC(=O)CCCCCCc1nc2ccc(-c3ccccc3)cc2[nH]1
methyl 7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanoate

Reactants

Nc1ccc(-c2ccccc2)cc1NC(=O)CCCCCCC(=O)[O-]
8-(4-aminobiphenyl-3-ylamino)-8-oxooctanoate
CC(=O)O
acetic acid

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Temperature
110°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated
  2. 2
    OtherThe residue was purified by biotage column chromatography

Procedure

To a solution of 8-(4-aminobiphenyl-3-ylamino)-8-oxooctanoate (120 mg, 0.34 mmol) in toluene was added a drop of acetic acid. The reaction was heated to 110° C. overnight and concentrated. The residue was purified by biotage column chromatography to give methyl 7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanoate (99 mg)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09381196B2uspto-grants-2016_07