Methyl iodide → HCID 22405461, compound

HRID 441216Notes

Reaction equation

HRID 441216 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[C:7](=[O:32])[N:8]([CH2:18][C:19]([NH:21][CH:22]([CH:29]([CH3:31])[CH3:30])[C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])=[O:20])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)=O.C(=O)([O-])[O-].[Na+].[Na+].CI.C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[CH3:3][NH:5][C:6]1[C:7](=[O:32])[N:8]([CH2:18][C:19]([NH:21][CH:22]([CH:29]([CH3:30])[CH3:31])[C:23](=[O:28])[C:24]([F:25])([F:26])[F:27])=[O:20])[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 10323328HCID 10323328, compound

Product 1

HCID 22405461HCID 22405461, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-(3-trifluoroacetylamino-2-oxo-6-phenyl -1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (Example 167 above) (200 mg)in dimethylformamide (2 mL) was added sodium carbonate (128 mg) and methyl iodide (130 μL). The mixture was stirred in a stoppered vessel overnight. Ethyl acetate and brine were added. The organic phase was separated, washed (brine), dried (MgSO4), and evaporated. Chromatography, eluting with dichloromethane:methanol (98:2), gave the title product (80 mg) as a white solid; TLC: Rf =0.15, dichloromethane:methanol (98:2); MS: m/z=506(M+1).

Workup

  1. customThe organic phase was separated
  2. washwashed (brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. washChromatography, eluting with dichloromethane:methanol (98:2)

Sources & evidence

ORD record
ord-69f551468d1943b68eb02679c1cad4b6
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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