Methyl iodide → HCID 10246185, compound

HRID 1813900Notes

Reaction equation

HRID 1813900 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([O:13]C)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](=[S:17])=S.[H-].[Na+].IC.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.[C:29]([O-])([O-])=O.[K+].[K+]>CS(C)=O.CN(C=O)C.C(Cl)Cl>[C:1]1([S:7]([C:10]2[C:11](=[O:13])[N:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]3=[N:22][C:29]=2[S:17][CH3:15])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

10

Reactant 6

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 104392-AminopyridineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 555619Methyl phenylsulfonyl acetate

Product 1

HCID 10246185HCID 10246185, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl phenylsulfonylacetate (5 g, 23.3 mmol) was mixed with carbon disulfide (1.77 g, 23.3 mmol) in anhydrous DMSO (100 ml) at room temperature. Sodium hydride (60% in mineral, 1.2 g, 48.9 mmol) was added portionwise. After stirring at room temperature for 1 hour iodomethane (6.9 g, 48.9 mmol) was added neat and stirred overnight. The reaction mixture was quenched with water and extracted with methylene chloride. The crude product was purified via flash chromatography. 670 mg of the product (˜2.1 mmol) was mixed with 2-aminopyridine (296 mg, 3.15 mmol) and K2CO3 (290 mg, 2.1 mmol) in DMF (2 ml). The reaction mixture was heated at 100° C. overnight then cooled to room temperature. The reaction mixture was diluted with methylene chloride (10 ml), washed with saturated aqueous NaCl, dried with Na2SO4 and concentrated. The product was an off white solid product, 30 mg, purified by preparative HPLC and flash chromatography.

Workup

  1. additionwas added neat
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with methylene chloride
  4. customThe crude product was purified via flash chromatography
  5. temperaturethen cooled to room temperature
  6. washwashed with saturated aqueous NaCl
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated
  9. custompurified by preparative HPLC and flash chromatography

Sources & evidence

ORD record
ord-2c2d79344acd4894b89a5d7191de4ccc
Source dataset
uspto-grants-2005_04
Patent number
US06875771B2

Reaction notes

Loading…