Phosphorus oxychloride → HCID 86641150, compound

HRID 1097415Notes

Reaction equation

HRID 1097415 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16]3[N:21]4[N:22]=[C:23]([C:25]5[CH:26]=[N+:27]([O-])[CH:28]=[CH:29][CH:30]=5)[N:24]=[C:20]4[N:19]=[CH:18][CH:17]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:28]1[N:27]=[CH:26][C:25]([C:23]2[N:24]=[C:20]3[N:19]=[CH:18][CH:17]=[C:16]([C:8]4[CH:9]=[CH:10][C:11]([O:12][CH:13]([F:15])[F:14])=[C:6]([O:5][CH2:4][CH:1]5[CH2:3][CH2:2]5)[CH:7]=4)[N:21]3[N:22]=2)=[CH:30][CH:29]=1.[Cl:34][C:26]1[C:25]([C:23]2[N:24]=[C:20]3[N:19]=[CH:18][CH:17]=[C:16]([C:8]4[CH:9]=[CH:10][C:11]([O:12][CH:13]([F:15])[F:14])=[C:6]([O:5][CH2:4][CH:1]5[CH2:3][CH2:2]5)[CH:7]=4)[N:21]3[N:22]=2)=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 24944540HCID 24944540, compound2×

Product 2

HCID 86641149HCID 86641149, compoundYield 30%HCID 86641150HCID 86641150, compoundYield 38%

Procedure

In POCl3, dissolved was 3-[7-{3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyri midine-2-yl]-pyridine-N-oxide (Compound 102) (2.7 g, 6.347 mmol), and the mixture was heated under reflux. The solvent was distilled under reduced pressure, and NaHCO3(aq.) was added to the residue. The mixture was extracted three times with EA, and the extract was washed twice with brine, dried over MgSO4, filtered and evaporated under reduced pressure to remove solvent. The mixture was purified via silica gel column chromatography (hexane/EA, 1/1) to obtain the desired compound, 2-(6-chloropyridin-3-yl)-7-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 104) (0.07 g, 30%) and 2-(2-chloropyridin-3-yl)-7-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 105) (0.09 g, 38%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. distillationThe solvent was distilled under reduced pressure, and NaHCO3(aq.)
  4. additionwas added to the residue
  5. extractionThe mixture was extracted three times with EA
  6. washthe extract was washed twice with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto remove solvent
  11. customThe mixture was purified via silica gel column chromatography (hexane/EA, 1/1)

Sources & evidence

ORD record
ord-4c0c64daf50341e0aaaca38ca4256658
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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