Phosphorus oxychloride → HCID 86605110, compound

HRID 545101Notes

Reaction equation

HRID 545101 reaction equation
Br.[F:2][C:3]([F:33])([F:32])[C:4]1[CH:5]=[C:6](O)[N:7]=[N:8][C:9]=1[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=2)[N:11]=1.O=P(Cl)(Cl)[Cl:36]>>[Cl:36][C:6]1[N:7]=[N:8][C:9]([C:10]2[N:11]=[C:12]3[C:17]([C:16]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=4)=[CH:15][CH:14]=[N:13]3)=[CH:18][CH:19]=2)=[C:4]([C:3]([F:33])([F:32])[F:2])[CH:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178419737HCID 178419737, compound

Product 1

HCID 86605110HCID 86605110, compound

Procedure

Dissolve 5-(trifluoromethyl)-6-(5-{[5-(trifluoromethyl)pyridin-2-yl]amino}-1,8-naphthyridin-2-yl)pyridazin-3-ol hydrobromide in neat POCl3 (20 mL). Heat the mixture at reflux for 4 hours. Cool and evaporate to dryness. Add toluene (25 mL) and remove the solvent under reduced pressure. Dissolve the residue in CH2Cl2 (30 mL) and sat. NaHCO3 (aq) (30 mL). Extract the aqueous phase with CH2Cl2 (3×30 mL). Combine, dry and evaporate the organic extracts to yield the title compound. LC/MS (MH+) 472.04.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 4 hours
  3. temperatureCool
  4. customevaporate to dryness
  5. customAdd toluene (25 mL) and remove the solvent under reduced pressure
  6. dissolutionDissolve the residue in CH2Cl2 (30 mL)
  7. extractionExtract the aqueous phase with CH2Cl2 (3×30 mL)
  8. customCombine, dry
  9. customevaporate the organic extracts

Sources & evidence

ORD record
ord-72ececb42d3842baa42a4897c539a04f
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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