Benzyl Bromide → HCID 67828573, compound

HRID 2379080Notes

Reaction equation

HRID 2379080 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]([OH:21])=[O:20])=[CH:13]2)=[O:8])[CH:2]=1.C(=O)([O-])O.[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[C:28]1([CH2:27][O:20][C:19]([C:14]2[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][CH2:10][NH:9][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:8])[CH:13]=2)=[O:21])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 18957857HCID 18957857, compound

Product 1

HCID 67828573HCID 67828573, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a 10 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet was added 1,6-dihydro-1-[2-(3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid (0.20 g, 0.70 mmol), dimethylformamide (5.0 ml), potassium hydrogen carbonate (0.175 g, 1.75 mmol), and benzyl bromide (0.082 ml, 0.69 mmol). The resulting suspension was heated in a 50° C. oil bath with stirring. After 2 hours, the solution was concentrated and the residue suspended in dichloromethane-methanol and water. The layers were separated and the organic layer washed with water and the combined aqueous layers back-extracted with dichloromethane (2X). The combined organic layers were dried (Na2SO4). Filtration, concentration, and purification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane) afforded the desired product as a white powder, MP: 154°-155° C.

Workup

  1. customTo a 10 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet
  2. concentrationthe solution was concentrated
  3. customThe layers were separated
  4. washthe organic layer washed with water
  5. extractionthe combined aqueous layers back-extracted with dichloromethane (2X)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationFiltration, concentration, and purification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-057e74632e2b41338384410f8466908c
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

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