Pyridine → HCID 117770672, compound

HRID 1526278Notes

Reaction equation

HRID 1526278 reaction equation
Cl.Cl.[Br:3][C:4]1[N:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1.N1C=CC=CC=1.[C:20](Cl)(=[O:22])[CH3:21].C(=O)([O-])O.[Na+]>O1CCCC1>[Br:3][C:4]1[N:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:20](=[O:22])[CH3:21])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 117770605HCID 117770605, compound

Product 1

HCID 117770672HCID 117770672, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-((6-bromopyridin-3-yl)oxy)ethanamine dihydrochloride obtained in Reference Example 5 (1.00 g), pyridine (1.12 mL) and tetrahydrofuran (20 mL) was added dropwise acetyl chloride (0.368 mL) at 0° C. The reaction mixture was stirred at room temperature for 5 hr, aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration, and washed with diisopropyl ether to give the title compound (0.792 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-ea9439b5e2804d95b4867067cbef185b
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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