Methanol → HCID 59497590, compound

HRID 1747383Notes

Reaction equation

HRID 1747383 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=[O:21])[CH:4]=[C:3]1[CH3:22].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO>CN(C=O)C.O>[CH3:28][O:27][C:23](=[O:26])[CH2:24][CH2:25][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:2]([CH3:1])[C:3]([CH3:22])=[CH:4]3)[C:13]1=[O:21]

Participants

7

Reactant 4

HCID 887MethanolHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 59497303HCID 59497303, compound

Product 1

HCID 59497590HCID 59497590, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(1,2-dimethyl-1H-indol-7-ylmethyl)-1,3-dihydro-benzimidazol-2-one (170 mg, 0.58 mmol) in DMF (3.0 mL) are added methyl acrylate (0.06 mL, 0.6 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.06 mL, 0.15 mmol). The resulting mixture is stirred at room temperature for 18 h after which time water (20 mL) was added. The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography using 20-50% EtOAc in Hexanes affords 90 mg (41%) of 3-[3-(1,2-dimethyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester.

Workup

  1. additionwas added
  2. extractionThe mixture is extracted with EtOAc (3×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-a1f1e747956647e5b7bf947bf744ac29
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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