1H-1,2,4-Triazole → HCID 66606898, compound

HRID 563638Notes

Reaction equation

HRID 563638 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[CH2:8]([O:10][C:11](=[O:39])[CH2:12][C:13]1[CH:14]=[C:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[CH2:31][N:32]([C:35](=[O:38])[CH2:36]Cl)[CH2:33][CH3:34])[C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[CH3:9]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.O>[CH2:8]([O:10][C:11](=[O:39])[CH2:12][C:13]1[CH:14]=[C:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][C:22]=2[CH2:31][N:32]([CH2:33][CH3:34])[C:35](=[O:38])[CH2:36][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[CH3:9]

Participants

8

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 66607317HCID 66607317, compound

Product 1

HCID 66606898HCID 66606898, compound

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,2,4-triazole (0.042 g, 0.61 mmol) in DMF at 0° C. was added sodium hydride (60% in mineral oil; 0.044 g, 1.1 mmol), and the mixture was stirred for 30 minutes. (2′-{[(2-Chloro-acetyl)-ethyl-amino]-methyl}-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.55 mmol) in DMF was added, followed by tetrabutylammonium iodide (0.1022 g, 0.06 mmol), and the reaction was warmed to room temperature and stirred for 1.5 hours. The mixture was diluted with EtOAc and H2O, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed three times with H2O, and then dried and concentrated, and the residue was purified by silica gel chromatography (40-90% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringstirred for 1.5 hours
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. washThe combined organic layers were washed three times with H2O
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (40-90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cff70b07dbaa4bfb9b4afe35482ab331
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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