Pyridine → HCID 57786284, compound

HRID 1628611Notes

Reaction equation

HRID 1628611 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=4[O:23][CH3:24])[C:12](=O)[CH2:13][N:7]3[C:6]=2[C:5]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:32])=O.N1C=CC=CC=1>>[Cl:32][C:12]1[N:11]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=2[O:23][CH3:24])[C:8]2[N:7]([CH:13]=1)[C:6]1[C:5]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=1[N:9]=2

Participants

4

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 57786339HCID 57786339, compound

Product 1

HCID 57786284HCID 57786284, compound

Conditions

Temperature
150 °C

Procedure

The mixture of 8-chloro-1-(4-chloro-2-methoxy-6-methylphenyl)-5-(1-ethylpropyl)-1H-imidazo[1,2-a]benzimidazol-2(3H)-one (31.8 mg, 0.0736 mmol) and phosphorus oxychloride (0.76 mL) and pyridine (11.9 μL, 0.147 mmol) was stirred at 150° C. for 5 days. After cooling, the mixture was concentrated in vacuo. The residue was neutralized with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give the title compound as an amorphous (8.7 mg, 0.0193 mmol, 26%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with brine (×1)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-1c4561b9007040caa8566a8f53dab5e6
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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