Methyl iodide → HCID 483539, compound

HRID 260480Notes

Reaction equation

HRID 260480 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[CH:16][C:15]([Cl:28])=[CH:14][CH:13]=2)=[O:9].I[CH3:30]>CO.O1CCCC1>[CH3:30][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[S:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:20])=[O:21])=[CH:16][C:15]([Cl:28])=[CH:14][CH:13]=2)=[O:9]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22401505HCID 22401505, compound

Product 1

HCID 483539HCID 483539, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a partial suspension of N-[(imidazol-2-yl)methyl] 3-phenylsulfonyl-5-chloroindole-2-carboxamide (Example 35) (42 mg, 0.1 mmol) in 1:1 methanol/tetrahydrofuran (4 mL) was added iodomethane (0.05 mL, 0.8 mmol). The reaction was stirred for three days at room temperature. The solvents were removed under reduced pressure, aq. NaHCO3 added and the product extracted into ethyl acetate/methanol. The organic layer was dried (Na2SO4), filtered, and the solvents evaporated. The residue was purified by chromatography and the product eluted with 3% methanol/chloroform. Appropriate fractions were combined, the solvents evaporated, and the residue triturated with methylene chloride to give pure product.

Workup

  1. customThe solvents were removed under reduced pressure, aq. NaHCO3
  2. additionadded
  3. extractionthe product extracted into ethyl acetate/methanol
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated
  7. customThe residue was purified by chromatography
  8. washthe product eluted with 3% methanol/chloroform
  9. customthe solvents evaporated
  10. customthe residue triturated with methylene chloride
  11. customto give pure product

Sources & evidence

ORD record
ord-6e51df6542b84bc78dc09e296c44b14d
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

Loading…