Methyl iodide → HCID 25188326, compound

HRID 1896752Notes

Reaction equation

HRID 1896752 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1.[CH3:24]I>CN(C)C=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([N:19]([CH3:24])[C:20](=[O:23])[CH2:21][CH3:22])=[CH:15][C:13]=3[N:14]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1141753HCID 1141753, compound

Product 1

HCID 25188326HCID 25188326, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To sodium hydride (15 mg, 0.37 mmol) under nitrogen at 0° C. was slowly added a solution of N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propionamide (100 mg, 0.33 mmol) in dimethylformamide (10 mL). After 10 min at 0° C., methyl iodide (56 μL, 0.37 mmol) was added, and the solution was left warming up to room temperature for 16 h. The mixture was then diluted with ethyl acetate, and then washed three times with water. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 50:50 v/v to afford 36.4 mg (35%) of the title compound (LCMS RT=7.00 min, MH+ 315.0)

Workup

  1. waitthe solution was left
  2. washwashed three times with water
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes 50:50 v/v

Sources & evidence

ORD record
ord-2ea4453712224a88a5605fa65eb54517
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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