Triethylamine → HCID 57677470, compound

HRID 492746Notes

Reaction equation

HRID 492746 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:18]([N:20]([CH2:23][CH3:24])[CH2:21]C)[CH3:19].ClC(OC1C=CC=CC=1)=[O:27].N1CCCC1>O1CCCC1>[N+:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:21]([N:20]3[CH2:23][CH2:24][CH2:19][CH2:18]3)=[O:27])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Product 1

HCID 57677470HCID 57677470, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-(4-nitrophenoxy)pyridine (490 mg) was dissolved in tetrahydrofuran (10 ml) under a nitrogen atmosphere, and then triethylamine (0.886 ml) and phenyl chloroformate (0.798 ml) were added dropwise, followed by stirring for 20 min. To the reaction mixture was added pyrrolidine (1.42 ml), followed by stirring for 40 min. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:3). Fractions containing the target compound were concentrated under a reduced pressure to give a residue, which was then dried in vacuum to provide the titled compound (639 mg, 91.8%) as a brown solid.

Workup

  1. stirringby stirring for 40 min
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order, and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:3)
  8. additionFractions containing the target compound
  9. concentrationwere concentrated under a reduced pressure
  10. customto give a residue, which
  11. customwas then dried in vacuum

Sources & evidence

ORD record
ord-16a311bb44e64f04acf80f09e23041ec
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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