Methyl iodide → HCID 68815178, compound

HRID 1436607Notes

Reaction equation

HRID 1436607 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:5]=1.IC.[C:23](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([N:15]([S:16]([CH3:19])(=[O:18])=[O:17])[CH3:23])[CH:5]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68814746HCID 68814746, compound

Product 1

HCID 68815178HCID 68815178, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-methanesulfonylamino-6-(methylpropylamino)-isonicotinic acid methyl ester (87 mg, 2.89 mmol) and iodomethane (0.27 mL, 4.33 mmoles) in DMF (10 mL). Add potassium carbonate (639 mg, 4.62 mmol) and tetrabutylammonium bromide (93 mg, 0.98 mmol) and stir at room temperature 1 h. Dilute with ethyl acetate (80 mL), wash with 10% aqueous potassium carbonate (2×15 mL), 0.1 N citric acid (2×15 mL), 1 N lithium chloride (2×15 mL) and saturated aqueous sodium chloride (15 mL).

Workup

  1. washwash with 10% aqueous potassium carbonate (2×15 mL), 0.1 N citric acid (2×15 mL), 1 N lithium chloride (2×15 mL) and saturated aqueous sodium chloride (15 mL)

Sources & evidence

ORD record
ord-f24233d4099447f5919bf0db02c51264
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…