Methyl iodide → HCID 67381073, compound

HRID 2409457Notes

Reaction equation

HRID 2409457 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5]([CH2:21][NH:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:4]=1.[C:29](=O)([O-])[O-].[K+].[K+].IC>C(#N)C>[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5]([CH2:21][N:22]([CH3:29])[N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67381226HCID 67381226, compound

Product 1

HCID 67381073HCID 67381073, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound (40 mg, 0.10 mmol) prepared in step 3 of Example 96 and potassium carbonate (22 mg, 0.15 mmol) were dissolved in acetonitrile (5 ml), added with iodo methane (0.008 ml, 0.12 mmol). The resulting mixture was heated to reflux temperature and stirred for 18 hours. The reaction mixture was poured into ice water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was then purified by flash column chromatography (dichloromethane:methanol=15:1) to obtain the title compound (3 mg, yield: 8%, yellow solid).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux temperature
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was then purified by flash column chromatography (dichloromethane:methanol=15:1)

Sources & evidence

ORD record
ord-73fe056dc90b45a4a49d7a9e087f18a4
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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