Tetrahydrofuran → HCID 59385070, compound

HRID 2356747Notes

Reaction equation

HRID 2356747 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6].[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+].O1CCCC1>C(OCC)(=O)C.O>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:3][CH2:4][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[O:6])=[O:19])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 1901858251746-82-8

Product 1

HCID 59385070HCID 59385070, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(2-aminoacetyl)pyridine dihydrochloride (50.00 g), 4-fluorobenzoylchloride (41.71 g) and sodium hydrogen carbonate (100.44 g) in ethyl acetate (1 liter) and water (0.6 liter) was stirred at room temperature for 2 hours. To the reaction mixture were added tetrahydrofuran (0.5 liter) and water (1 liter), and the organic layer was collected. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was triturated with ethyl acetate to obtain 3-[2-(4-fluorobenzoyl)aminoacetyl]pyridine (40.87 g) as pale yellowish powder.

Workup

  1. customthe organic layer was collected
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-6496f246c6bb435aac00c0cc5267eb98
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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