Triethylamine → N-[4-(4-nitrophenoxy)-2-pyridinyl]-1-pyrrolidinecarboxamide

HRID 492746노트

반응식

HRID 492746 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 57677470N-[4-(4-nitrophenoxy)-2-pyridinyl]-1-pyrrolidinecarboxamide수율 91.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-16a311bb44e64f04acf80f09e23041ec
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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