Pyridine → HCID 68695860, compound

HRID 2236837Notes

Reaction equation

HRID 2236837 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12](N)[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.N([O-])=O.[Na+].[FH:28]>>[F:28][C:12]1[N:13]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:9]=[CH:10][C:11]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 4

HCID 1049PyridineHCID 14917Hydrofluoric AcidHCID 21354525HCID 21354525, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 68695860HCID 68695860, compound

Conditions

Temperature
0 °C

Procedure

A solution of 6-(4-methylpiperazin-1-yl)-3-nitropyridin-2-amine (1.2 g, 5.0 mmol) in hydrogen fluoride.pyridine (15 mL) is cooled to 0° C. in an ice-water bath. Sodium nitrite (0.36 g, 5.2 mmol) is added in a single portion, and the mixture is stirred for 30 minutes at 0° C. The bath is removed and the mixture is heated for 15 minutes in an oil bath on a 70° C. hot plate. After cooling to room temperature, the reaction mixture is poured onto ice (50 g), neutralized with saturated aqueous sodium hydrogen carbonate solution, and basified with 10 N sodium hydroxide solution. The mixture is extracted 3× with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Eighty-percent of the crude residue is purified by reverse-phase HPLC to give 1-(6-fluoro-5-nitropyridin-2-yl)-4-methylpiperazine.trifluoroacetic acid salt (0.40 g, 29%).

Workup

  1. customThe bath is removed
  2. temperaturethe mixture is heated for 15 minutes in an oil bath on a 70° C. hot plate
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture is poured onto ice (50 g)
  5. extractionThe mixture is extracted 3× with dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customEighty-percent of the crude residue is purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-64a033e355b7462980bad059ef1923d5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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