Triethylamine → HCID 10221864, compound

HRID 547698Notes

Reaction equation

HRID 547698 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](O)[CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].[CH2:29]([N:31](CC)CC)[CH3:30].CS(Cl)(=O)=O>O1CCCC1.C(=O)(O)[O-].[Na+]>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:30][C:29]#[N:31])[CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22318959HCID 22318959, compound

Product 1

HCID 10221864HCID 10221864, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(2-Cyanophenyl)-5-(2-pyridyl)-1-(3-hydroxyphenyl)-1,2-dihydropyridin-2-one (53 mg) was dissolved in 2 ml of tetrahydrofuran, then 60 ml of triethylamine and 20 ml of methanesulfonyl chloride were added thereto with ice cooling and the mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate and the extract was dried over anhydrous magnesium sulfate. The drying agent was filtered off, the filtrate was concentrated in vacuo, the resulting residue was dissolved in 1 ml of dimethyl sulfoxide, 3 mg of sodium cyanide were added and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate, washed with an aqueous solution of sodium bicarbonate and a saturated saline solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the filtrate was concentrated in vacuo and the resulting crude crystals were recrystallized from ethyl acetate-diethyl ether-hexane to give 12 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionthe resulting residue was dissolved in 1 ml of dimethyl sulfoxide
  6. addition3 mg of sodium cyanide were added
  7. stirringthe mixture was stirred at room temperature for 1 hour
  8. additionThe reaction solution was diluted with ethyl acetate
  9. washwashed with an aqueous solution of sodium bicarbonate
  10. dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
  11. filtrationThe drying agent was filtered off
  12. concentrationthe filtrate was concentrated in vacuo
  13. customthe resulting crude crystals were recrystallized from ethyl acetate-diethyl ether-hexane

Sources & evidence

ORD record
ord-55a29502643340d08676f1044b5326c8
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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