Methyl iodide → HCID 15452331, compound

HRID 1066875Notes

Reaction equation

HRID 1066875 reaction equation
IC.[C:3](=O)([O-])[O-].[K+].[K+].[Br:9][C:10]1[CH:24]=[N:23][C:13]2[NH:14][C:15](=[S:22])[N:16]([CH2:19][CH2:20][CH3:21])[C:17](=[O:18])[C:12]=2[CH:11]=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[Br:9][C:10]1[CH:24]=[N:23][C:13]2[N:14]=[C:15]([S:22][CH3:3])[N:16]([CH2:19][CH2:20][CH3:21])[C:17](=[O:18])[C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 21196274HCID 21196274, compound

Product 1

HCID 15452331HCID 15452331, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of iodomethane (1.33 g, 0.58 mL), 8.7 g potassium carbonate and 1.88 g of the title compound of Step B was stirred at room temperature in 50 mL of dimethylformamide for 3 h. A 1 mL portion of saturated aqueous NaHCO3 was added and the reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was partitioned between 200 mL each of methylene chloride and water, and the organic layer was removed. Further washing of the organic phase with water and saturated aqueous NaCl followed by drying (Na2SO4) and concentration under reduced pressure delivered 1.8 g of the crude product. This material was then subjected to silica gel chromatography using 70:30 hexane:ethyl acetate as eluant to afford 1.48 g of the title compound of Step C, a compound of the invention, as a white solid melting at 124-127° C. 1H NMR (400 MHz, CDCl3): δ 1.03 (t,3H), 1.76-1.90 (m,2H), 2.7 (s,3H), 4.1 (t,2H), 8.63 (s,1H), 8.89 (s,1H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  2. customThe resulting residue was partitioned between 200 mL each of methylene chloride and water
  3. customthe organic layer was removed
  4. washFurther washing of the organic phase with water and saturated aqueous NaCl
  5. customby drying
  6. concentration(Na2SO4) and concentration under reduced pressure

Sources & evidence

ORD record
ord-52a860b2991b4fa082ce65ff826ddb50
Source dataset
uspto-grants-2001_06
Patent number
US06245770B1

Reaction notes

Loading…