Ammonia → 6-(4-Isopropyl-piperazin-1-yl)-pyridin-3-yl-amine

HRID 409695노트

반응식

HRID 409695 반응식
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CCO.O.N>[Fe].CC(O)=O>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 339957181-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

생성물 1

HCID 434620426-(4-Isopropyl-piperazin-1-yl)-pyridin-3-yl-amine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
90 °C

실험 절차

A mixture of iron powder (1.4 g, 25.3 mmol, 4 equiv), 1-isopropyl-4-(5-nitro-pyridin-2-yl)piperazine (1.58 g, 6.32 mmol), EtOH (20 mL), H2O (5 mL), and AcOH (2.5 mL) is stirred for 2 h at 90° C., allowed to cool to RT, basified by addition of aqueous ammonia, filtered through a pad of celite and partially concentrated to remove EtOH. The aqueous residue is saturated with sodium chloride and extracted with EtOAc and DCM. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1) to afford the title compound as a purple solid: ESI-MS: 221.1 [MH]+; TLC: Rf=0.20 (DCM/MeOH/NH3aq, 91:8:1).

후처리

  1. temperatureto cool to RT
  2. filtrationfiltered through a pad of celite
  3. concentrationpartially concentrated
  4. customto remove EtOH
  5. extractionextracted with EtOAc and DCM
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1)

출처 및 근거

ORD 기록
ord-a1a900b102474e85bb00a0a23552f74b
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759517B2

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