Methyl iodide → HCID 53985471, compound

HRID 1459402Notes

Reaction equation

HRID 1459402 reaction equation
[C:1]12([NH:11][C:12](=[O:30])[C:13]([CH2:28][OH:29])([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH3:33]I>O1CCCC1>[C:1]12([NH:11][C:12](=[O:30])[C:13]([CH2:28][O:29][CH3:33])([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53924158HCID 53924158, compound

Product 1

HCID 53985471HCID 53985471, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well-stirred suspension of N-adamantan-1-yl-2-hydroxymethyl-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propionamide (40 mg, 0.1 mmol) in anhydrous tetrahydrofuran (0.50 ml), sodium hydride (7.8 mg of 60% mineral oil dispersion; 0.2 mmol of sodium hydride) was added. After stirring at ambient temperature for 30 minutes, methyl iodide (12.5 μl, 0.2 mmol) was added. After stirring for 2 hours at ambient temperature, the reaction was quenched by the addition of water/methylene chloride (10 ml of each). The mixture was then extracted twice with 10 ml portions of methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to an oil (60 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/ethyl acetate=1:9 in volume) afforded the title compound (free base) as an amorphous solid (16 mg).

Workup

  1. additionwas added
  2. stirringAfter stirring for 2 hours at ambient temperature
  3. customthe reaction was quenched by the addition of water/methylene chloride (10 ml of each)
  4. extractionThe mixture was then extracted twice with 10 ml portions of methylene chloride
  5. dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
  6. concentrationconcentrated in vacuo to an oil (60 mg)
  7. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/ethyl acetate=1:9 in volume)

Sources & evidence

ORD record
ord-c24baa278c494a269b425deb81489b62
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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