Pyridine → HCID 5275155, compound

HRID 1988807Notes

Reaction equation

HRID 1988807 reaction equation
[C:1]1([N:11]2[CH:15]=[N:14][NH:13][C:12]2=[S:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29])=[O:20].N1C=CC=CC=1>CS(C)=O.O>[C:1]1([N:11]2[CH:15]=[N:14][N:13]=[C:12]2[S:16][CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2207872-bromo-n-(2-nitrophenyl)acetamideHCID 28887991HCID 28887991, compound

Product 1

HCID 5275155HCID 5275155, compoundYield 2.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2,4-dihydro-4-(1-naphthalenyl)-3H-1,2,4-triazole-3-thione (129 mg, 0.50 mmol) in DMSO (2 mL) was added slowly to a solution of 2-bromo-N-(2-nitrophenyl)acetamide (113 mg, 0.50 mmol) and pyridine (121 μL, 1.49 mmol) in DMSO (1 mL) at room temperature. The mixture was stirred at room temperature for 18 h, then diluted with water and extracted with EtOAc (50 mL). The organic layer was washed with water (3×) and brine, dried (MgSO4), filtered and concentrated under reduced pressure. A mixture of Et2O and hexane (1:1) was added, the resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by HPLC using a gradient of MeCN/H2O containing TFA (0.06%) (CombiPrep ODS-AQ 50×20 mm, 5μ, 120 Å). The pure fractions were combined and concentrated to give the title compound (4.5 mg, 2% yield).

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. washThe organic layer was washed with water (3×) and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionA mixture of Et2O and hexane (1:1)
  7. additionwas added
  8. filtrationthe resulting suspension was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by HPLC
  11. additioncontaining TFA (0.06%) (CombiPrep ODS-AQ 50×20 mm, 5μ, 120 Å)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-3de7a3f32d4c4aca8d9eab505dd60f75
Source dataset
uspto-grants-2010_01
Patent number
US07642277B2

Reaction notes

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