Methyl iodide → HCID 68430955, compound

HRID 2092093Notes

Reaction equation

HRID 2092093 reaction equation
[OH:1][C:2]1[C:3](=[O:25])[N:4]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].CI.[C:28](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH3:28][O:1][C:2]1[C:3](=[O:25])[N:4]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178461480HCID 178461480, compound

Product 1

HCID 68430955HCID 68430955, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

4-Hydroxy-2-(tetrahydro-2H-pyran-2-yl)-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (250 mg, 0.72 mmol) in N,N-dimethylformamide (2.5 mL) was mixed with methyl iodide (70 μL, 0.76 mmol) and potassium carbonate (104 mg, 0.76 mmol) at room temperature and stirred at 65° C. for 1 hour. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to give the desired product (154 mg, 59% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-3406803cb05c4953b1f982e1d91ec19b
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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