Methyl iodide → HCID 10050637, compound

HRID 1760569Notes

Reaction equation

HRID 1760569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:32])([C:26]2[N:27]([CH3:31])[CH:28]=[N:29][CH:30]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[C:20]2[S:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:35]I>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:32])([C:26]2[N:27]([CH3:31])[CH:28]=[N:29][CH:30]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:35])[C:14](=[O:19])[CH:13]=[C:12]3[C:20]2[S:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 12133218HCID 12133218, compound

Product 1

HCID 10050637HCID 10050637, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(5-methyl-thiophen-2-yl)-1H-quinolin-2-one (115 mg, 0.248 mmol) in THF (6.6 ml) was added a 40% aqueous NaOH (3.3 ml), benzyltriethylammonium chloride (28 mg. 0.124 mmol) and a solution of methyl iodide (0.017 ml, 0.273 mmol) in THF (0.05 ml). The reaction mixture was stirred at ambient temperature for 1.5 hours after which time it was partitioned between ethyl acetate and 10% aqueous potassium carbonate. The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give the crude product. It was chromatographed on silica gel with MeOH—CHCl3—NH4 (1:99:0.1) as eluents to afford the title compound as a white solid (68 mg, 0.143 mmol, 58% yield).

Workup

  1. customwas partitioned between ethyl acetate and 10% aqueous potassium carbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customto give the crude product
  6. customIt was chromatographed on silica gel with MeOH—CHCl3—NH4 (1:99:0.1) as eluents

Sources & evidence

ORD record
ord-ee00fbb5bb934375a589f8a186d6fcb6
Source dataset
uspto-grants-2005_01
Patent number
US06844357B2

Reaction notes

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