Methyl iodide → HCID 69355273, compound

HRID 1744244Notes

Reaction equation

HRID 1744244 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]([C:11]1[C:12](=[O:20])[NH:13][CH:14]=[C:15]([C:17]([OH:19])=[O:18])[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:29]>CN(C)C=O.O>[CH2:21]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([C:11]1[C:12]([O:20][CH3:29])=[N:13][CH:14]=[C:15]([C:17]([OH:19])=[O:18])[CH:16]=1)=[O:10])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 69354528HCID 69354528, compound

Product 1

HCID 69355273HCID 69355273, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g (1.4 mmol) 2-Oxo-1,2-dihydro-pyridine-3,5-dicarboxylic acid bis-benzylamide in 10 mL of N,N-dimethylformamide (DMF) was added 0.25 g (1.9 mmol) diisopropylethylamine amine followed by 0.19 g (1.4 mmol) iodomethane. The resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with saturated aqueous NaCl solution, and dried over MgSO4. The product was crystallized from ethyl acetate, providing 0.24 g (46% yield) of the title compound. MS: m/z (APCI, AP+) 376.3 [M−]+. CHN Analysis: Calcd: C, 70.38; H, 5.64; N, 11.19. Found: C, 70.05; H, 5.49; N, 10.89.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe combined organic extracts were washed with saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d9f3a4e69cdf4e5ea6650e5620fe1caa
Source dataset
uspto-grants-2006_03
Patent number
US07015237B2

Reaction notes

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