Water → HCID 58497412, compound

HRID 2175190Notes

Reaction equation

HRID 2175190 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[NH:12][C:11]1=[O:19])[CH2:6][CH2:7][CH3:8])[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][N+](C)(C)C)=[CH:24]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:9][N:10]1[C:14]2=[N: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])[CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 17836486((1,4-Dimethylindole-3-yl)methyl)trimethylammonium iodideHCID 58497373HCID 58497373, compound

Product 1

HCID 58497412HCID 58497412, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-ylmethyl)-pentanoic acid ethyl ester (50 mg, 0.18 mmol) in DMF (5 ml) were added (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium iodide (75 mg, 0.22 mmol) and K2CO3 (75 mg, 0.54 mmol) at room temperature under nitrogen atmosphere. The solution was heated to 60° C. for 3 hours. The solution was cooled and poured into water (100 ml) and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc twice. The combined organics were dried (MgSO4), filtered and concentrated. The remaining residue was purified via silica gel flash column chromatography (Companion, 4 g silica gel, 20-100% EtOAc/hexanes) to give 85 mg (108%) of the title compound.

Workup

  1. temperatureThe solution was cooled
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc twice
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe remaining residue was purified via silica gel flash column chromatography (Companion, 4 g silica gel, 20-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-eb6828c05f164a53b8af6bdd4152fe2f
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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