Dimethyl Sulfate → HCID 54520530, compound

HRID 2379085Notes

Reaction equation

HRID 2379085 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH:14][C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:6]=1)=[O:4].[H-].[Na+].[CH3:25]OS(OC)(=O)=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][N:14]([C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH3:25])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 54154763HCID 54154763, compound

Product 1

HCID 54520530HCID 54520530, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round bottomed 25 ml flask fitted with a magnetic stirrer bar and nitrogen inlet was added 1,6-dihydro-l-[2-(3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid methyl ester (0.211 g, 0.70 mmol) and dimethylformamide (7.0 ml). At room temperature with stirring, sodium hydride (0.018 g, 0.77 mmol, 98% dry) was added. After 45 minutes, the reaction was quenched with dimethylsulfate (0.073 ml, 0.78 mmol). Stirring was continued for 3.75 hours at which time the mixture was concentrated. The crude product was purified by medium pressure liquid chromotography (silica gel, 3% methanol/dichloromethane) and triturated with ether to give the product, MP: 120°-122° C.

Workup

  1. customTo a round bottomed 25 ml flask fitted with a magnetic stirrer bar and nitrogen inlet
  2. stirringStirring
  3. waitwas continued for 3.75 hours at which time
  4. concentrationthe mixture was concentrated
  5. customThe crude product was purified by medium pressure liquid chromotography (silica gel, 3% methanol/dichloromethane)
  6. customtriturated with ether
  7. customto give the product, MP: 120°-122° C.

Sources & evidence

ORD record
ord-104f5974ca4744df98ca909f4e059bf6
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

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