Phosphorus oxychloride → HCID 57929911, compound

HRID 1930088Notes

Reaction equation

HRID 1930088 reaction equation
[NH2:1][N:2]1[C:6]([CH:7]([CH3:9])[CH3:8])=[N:5][N:4]=[C:3]1[SH:10].[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]1[N:20]=[C:21]2[N:25]([C:26]=1[C:27](O)=O)[CH:24]=[CH:23][O:22]2.O=P(Cl)(Cl)Cl>C(Cl)Cl>[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]1[N:20]=[C:21]2[N:25]([C:26]=1[C:27]1[S:10][C:3]3=[N:4][N:5]=[C:6]([CH:7]([CH3:9])[CH3:8])[N:2]3[N:1]=1)[CH:24]=[CH:23][O:22]2

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 57929958HCID 57929958, compoundHCID 178440399HCID 178440399, compound

Product 1

HCID 57929911HCID 57929911, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 5 mL round-bottomed flask equipped with a reflux condenser outfitted with a nitrogen inlet adapter was charged with 4-amino-5-isopropyl-4H-1,2,4-triazole-3-thiol (0.15 g, 0.95 mmol, Enamine) and 6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole-5-carboxylic acid (0.25 g, 0.95 mmol) in POCl3 (3.5 mL, 38 mmol) to give a tan suspension. The reaction mixture was heated at about reflux for about 18 h, allowed to cool, and then poured over stirring ice water. The mixture was diluted with DCM and the layers were separated. The organic layer was concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to provide a white solid (0.055 g) which was dissolved in a minimal amount of hot ACN and left to cool to ambient temperature for about 2 h. The resulting crystals were isolated by filtration, washed with ACN, and dried under vacuum to give the title compound (0.020 g, 5%): LC/MS (Table 1, Method b) Rt=1.95 min; MS m/z: 387.2 (M+H)+.

Workup

  1. customA 5 mL round-bottomed flask equipped with a reflux condenser
  2. customoutfitted with a nitrogen inlet adapter
  3. customto give a tan suspension
  4. temperatureThe reaction mixture was heated at
  5. temperatureabout reflux for about 18 h
  6. temperatureto cool
  7. additionpoured
  8. customthe layers were separated
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customThe resulting residue was purified via silica gel chromatography
  11. washeluting with a gradient of 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-131ce47b2c0046aabaf841619b25ad86
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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