Tetrahydrofuran → HCID 1070379, compound

HRID 391545Notes

Reaction equation

HRID 391545 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].C1COCC1.[C:14]([C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1)#[CH:15]>CCN(CC)CC>[C:14]([C:16]1[CH:17]=[C:18]([NH:22][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH:19]=[CH:20][CH:21]=1)#[CH:15]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789282-Thiophenecarbonyl chlorideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 1070379HCID 1070379, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

A dry 25 mL flask was charged with thiophene-2-carbonyl chloride and THF (5 mL) was added. 3-Ethynyl-phenylamine (0.905 g, 3.59 mmol) was added to the THF solution of the acid chloride followed by NEt3, and the mixture was allowed to stir at 55° C. The reaction mixture was then allowed to cool to room temperature and extracted with EtOAc (˜10 mL), 1M HCl (˜10 mL), followed by brine (˜10 mL). The combined organic extracts were combined and dried over anhydrous Na2SO4(s) and the concentrated. The crude residue was purified by chromatography (silica gel, gradient elution EtOAc/Hexanes 0 to 50%). The product containing fractions were concentrated to give the title compound as a tan solid (0.33 mg, 1.45 mmol, 85%).

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. extractionextracted with EtOAc (˜10 mL), 1M HCl (˜10 mL)
  4. dry with materialdried over anhydrous Na2SO4(s)
  5. customThe crude residue was purified by chromatography (silica gel, gradient elution EtOAc/Hexanes 0 to 50%)
  6. additionThe product containing fractions
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-242f11cecf1c44939decf14b0bcebea3
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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