Triethylamine → HCID 67260280, compound

HRID 2359027Notes

Reaction equation

HRID 2359027 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:16]([NH:20][NH2:21])([CH2:18][CH3:19])[CH3:17].[CH2:22](N(CC)CC)C>ClCCl>[CH:16]([N:20]1[CH:22]=[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:21]1)([CH2:18][CH3:19])[CH3:17].[CH:16]([N:20]1[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:22]=[N:21]1)([CH2:18][CH3:19])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 547690sec-ButylhydrazineHCID 65583291HCID 65583291, compound

Product 2

HCID 67260280HCID 67260280, compoundYield 21%HCID 67260571HCID 67260571, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(5-chloro-2-thienyl)-2-(pyridin-4-yl)ethanone (0.68 mmol), secbutylhydrazin (1.37 mmol) and triethylamine (1.37 mmol) in 5 mL dichloromethane was refluxed for 2.5 h. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1) to afford 37 mg of 4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (16% yield) and 48 mg of 4-[1-sec-butyl-5-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (21% yield).

Workup

  1. temperaturewas refluxed for 2.5 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1)

Sources & evidence

ORD record
ord-836c52c166684ccfa282695d0e5143ee
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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