Potassium Carbonate → HCID 11199618, compound

HRID 346508Notes

Reaction equation

HRID 346508 reaction equation
[N:1]1([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]4[N:22]=[C:21](O)[CH:20]=[CH:19][CH:18]=4)=[N:15][N:16]=3)[N:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Br)(Br)[Br:25].C(=O)([O-])[O-].[K+].[K+]>>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Br:25])[N:22]=4)=[N:15][N:16]=3)[N:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 178515988HCID 178515988, compound

Product 1

HCID 11199618HCID 11199618, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 6-(6-azepan-1-yl-1,2,4-triazolo[4,3-b]pyridazin-3-yl)pyridine-2-ol (700 mg) and phosphorus tribromide (7 ml) was stirred at 130° C. for 6 hours. After allowing to cool to room temperature, an ice-water was added, and the mixture was neutralized with saturated aqueous solution of potassium carbonate, and extracted with chloroform. The extract was washed with saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: chloroform:methanol=98:2) and recrystallized from ethanol to obtain 6-azepan-1-yl-3-(6-bromopyridin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine (240 mg) as colorless crystals.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated aqueous solution of sodium hydrogen carbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (eluent: chloroform:methanol=98:2)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-eae19cea7f3d4f7b8a127e980f2f2c04
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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