Sodium Hydroxide → HCID 178516190, compound

HRID 510372Notes

Reaction equation

HRID 510372 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([C:21]([F:24])([F:23])[F:22])[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=3[Cl:20])=[C:4]2[N:3]=1.[OH-:25].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([OH:25])[N:5]2[N:9]=[C:10]([C:21]([F:24])([F:23])[F:22])[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=3[Cl:20])=[C:4]2[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86724869HCID 86724869, compound

Product 1

HCID 178516190HCID 178516190, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 5,7-dichloro-3-[(2,3-dichlorophenyl)methyl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (0.83 g, 2.0 mmol) in THF (10 mL) and water (2.5 mL) was added 1.6 mL of 6N sodium hydroxide solution. Reaction mixture was stirred at 45° C. overnight. Reaction mixture was concentrated down to s small volume, and diluted with 10 mL of icy water. The pH of reaction solution was adjusted to ˜7, and extracted with ethyl acetate (35 mL×2). Combined organic layers were dried over anhydrous sodium sulfate, and concentrated to dryness. The crude material was purified with column chromatography. Product was obtained and used without further purification in the next step. (0.273 g, 34%); LC/MS: MS (ES+) m/e 396 (MH+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. concentrationwas concentrated down to s small volume
  4. additiondiluted with 10 mL of icy water
  5. customThe pH of reaction solution
  6. extractionextracted with ethyl acetate (35 mL×2)
  7. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe crude material was purified with column chromatography
  10. customProduct was obtained
  11. customused without further purification in the next step

Sources & evidence

ORD record
ord-3b17943ead664e6bbc5aa4d09ff15b9f
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

Loading…