Ammonium Chloride → 3-cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

HRID 79388

반응식

HRID 79388 반응식
[CH:1]1([C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[N+:13]([O-])=O)[N:6]([CH2:16][C:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=3)[N:5]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH:1]1([C:4]2[C:12]3[C:11]([NH2:13])=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]([CH2:16][C:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=3)[N:5]=2)[CH2:2][CH2:3]1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 708150333-cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole

생성물 1

HCID 672595033-cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine수율 103.8%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 3-cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (7.55 g, 24.3 mmol) in EtOH/H2O (70 mL/15 mL) was added iron powder (27.1 g, 485 mmol) and NH4Cl (1.30 g, 24.3 mmol). The reaction mixture was heated to reflux for 3 hours. The mixture was cooled to 60° C. and filtered through a pad of Celite washing with a 20:1 EtOH/Et3N (300 mL) and 1:1 MeOH/DCM (300 mL). The filtrate was concentrated under reduced pressure. The residue was dissolved in EtOAc (300 mL), washed with saturated NaHCO3 solution, dried (Na2SO4) and concentrated under reduced pressure to give the product (7.1 g).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of Celite
  4. washwashing with a 20:1 EtOH/Et3N (300 mL) and 1:1 MeOH/DCM (300 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in EtOAc (300 mL)
  7. washwashed with saturated NaHCO3 solution
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6b42dcc393e94733ab63114fcc4f6fb2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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