Water → HCID 59497255, compound

HRID 1747369Notes

Reaction equation

HRID 1747369 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:24])=[C:12]2[C:8]([C:9]([CH3:27])=[C:10]([CH3:26])[N:11]2[CH3:25])=[CH:7][CH:6]=1)=[O:4].[CH3:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32].[OH-].[CH2:35]([N+](C)(C)C)C1C=CC=CC=1.O>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH2:32][CH2:31][C:30]([O:29][CH2:28][CH3:35])=[O:33])[C:16]2=[O:24])=[C:12]2[C:8]([C:9]([CH3:27])=[C:10]([CH3:26])[N:11]2[CH3:25])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 59497374HCID 59497374, compound

Product 1

HCID 59497255HCID 59497255, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1,2,3-Trimethyl-7-(2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1H-indole-6-carboxylic acid methyl ester (70 mg, 0.19 mmol) in DMF (10 mL) was added the methylacrylate (0.035 mL, 0.39 mmol) followed by the benzyltrimethylammonium hydroxide (40% in MeOH) (0.13 mL, 0.29 mmol). The resulting solution was stirred at ambient temperature for 2 h after which time the reaction appeared complete. The reaction was poured into water and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (2×). The combined organics were dried with MgSO4 and was filtered, concentrated. The residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the product 7-[3-(2-Ethoxycarbonyl-ethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl]-1,2,3-trimethyl-1H-indole-6-carboxylic acid methyl ester (66 mg, 76%) as a colorless oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×)
  3. dry with materialThe combined organics were dried with MgSO4
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customThe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-54fd7a0feb1d46be8c11cca6067d260a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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