Methyl iodide → HCID 68830854, compound

HRID 1986504Notes

Reaction equation

HRID 1986504 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:35][CH:36]([CH3:38])[CH3:37])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:35][CH:36]([CH3:38])[CH3:37])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)=[CH:17][C:16]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:39])=[O:33])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 51050037HCID 51050037, compound

Product 1

HCID 68830854HCID 68830854, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]hexanoic acid (885 mg, 1.71 mmol) and potassium carbonate (469 mg, 3.39 mmol) in N,N-dimethylformamide (40 ml) was added methyl iodide (291 mg, 2.05 mmol), and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give methyl 6-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]hexanoate (870 mg, yield 96%) as white crystals. Subsequently, methyl 6-[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]hexanoate was synthesized by a method similar to the method shown in Example 32(2).

Workup

  1. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-883c91749c7f4507930fc790b5e08497
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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