Triethylamine → 1-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-ylmethyl]-pyrrolidin-2-one

HRID 1661939Notes

Reaction equation

HRID 1661939 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([CH2:23][NH2:24])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C([O:29][C:30](=O)[CH2:31][CH2:32][CH2:33]Br)C.C(N(CC)CC)C>CC(C)CCO>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([CH2:23][N:24]4[CH2:33][CH2:32][CH2:31][C:30]4=[O:29])=[CH:22][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrateHCID 57772089C-[2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methylamine

Product 1

HCID 577719861-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-ylmethyl]-pyrrolidin-2-oneYield 33.2%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A solution of 50 mg (0.143 mmol) C-[2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methylamine, 28 mg (0.143 mmol) ethyl-4-bromobutyrate and 28 μl (0.2 mmol) triethylamine in 4 ml 3-methyl-1-butanol is stirred at reflux temperature for 8 h. Then the reaction mixture is poured on water and extracted (3×) with EtOAc. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (EtOAc:MeOH=98:2) to afford 20 mg of the title compound as a colorless oil.

Workup

  1. temperatureat reflux temperature for 8 h
  2. additionThen the reaction mixture is poured on water
  3. extractionextracted (3×) with EtOAc
  4. washThe combined organic layers are washed with water (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (EtOAc:MeOH=98:2)

Sources & evidence

ORD record
ord-f474c755ecc542e480d85a3c5e186589
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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