4-Toluenesulfonyl chloride → Tert-butyl[4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl]carbamate

HRID 452761Notes

Reaction equation

HRID 452761 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[C:12]([C:14]([NH:16][NH:17][C:18](=[O:28])[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=O)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[O:28][C:18]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)=[N:17][N:16]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86640025Tert-butyl [4-[[2-[3-(3-fluorophenyl)propanoyl]hydrazino]carbonyl]-2-pyridyl]carbamate

Product 1

HCID 86640041Tert-butyl[4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl]carbamateYield 73.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl[4-[[2-[3-(3-fluorophenyl)propanoyl]hydrazino]carbonyl]-2-pyridyl]carbamate (1.00 g, 2.48 mmol), p-toluenesulfonyl chloride (946 mg, 4.96 mmol) and triethylamine (1.72 mL, 12.4 mmol) in tetrahydrofuran (30 mL) was heated under reflux for 17 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-0/100), and recrystallized from ethyl acetate to give the title compound (0.70 g, yield 73%) as colorless crystals.

Workup

  1. temperatureunder reflux for 17 hr
  2. temperatureAfter cooling
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0f05802a4fd54999a00b500e3ff0a0d9
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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