Water → (S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747376Notes

Reaction equation

HRID 1747376 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2].[I-].[CH3:22][N:23]1[C:31]2[C:26](=[C:27]([CH3:32])[CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:33]CN(C)C)=[CH:24]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:33][C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[N:23]([CH3:22])[CH:24]=2)[C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 59497467(S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 86645718(1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-amine iodide salt

Product 1

HCID 59497309(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (700 mg, 2.5 mmol) in DMF (50 mL) were added (1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-amine iodide salt (1.3 g, 3.8 mmol) and K2CO3 (700 mg, 5.1 mmol) at room temperature under nitrogen atmosphere. The solution was heated to 100 C for 4 hours. The solution was cooled down and water was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The solution was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester (737 mg, 67%) as a yellow foam.

Workup

  1. temperatureThe solution was heated to 100 C for 4 hours
  2. temperatureThe solution was cooled down
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialthe combined organic layer was dried with MgSO4
  5. filtrationThe solution was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-a2fb73ddf6e34d19a69eb33f1174d82b
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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