Ammonium Chloride → 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazole-4-amine

HRID 79423

반응식

HRID 79423 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:22]=[CH:21][CH:20]=[C:19]([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:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=3)[N:5]=2)[CH2:2][CH2:3]1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 672608093-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

생성물 1

HCID 672592723-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazole-4-amine수율 84.9%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (22.01 g, 71.38 mmol) in EtOH/H2O (200 mL/50 mL) was added iron powder (79.73 g, 1428 mmol) and NH4Cl (3.818 g, 71.38 mmol). The reaction mixture was heated to reflux for three hours, cooled to 60° C. and filtered through a pad of Celite. The pad of Celite was washed with 20:1 EtOH/Et3N (800 mL) and 1:1 MeOH/DCM (600 mL). The combined filtrate was concentrated under reduced pressure. The residue was dissolved in EtOAc (800 mL), washed with saturated NaHCO3 aqueous solution, dried (Na2SO4) and concentrated under reduced pressure to give the product (16.87 g).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for three hours
  3. filtrationfiltered through a pad of Celite
  4. washThe pad of Celite was washed with 20:1 EtOH/Et3N (800 mL) and 1:1 MeOH/DCM (600 mL)
  5. concentrationThe combined filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in EtOAc (800 mL)
  7. washwashed with saturated NaHCO3 aqueous solution
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-23a6bef378da49d3a527ffbf1fd547a2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

연결된 노트

불러오는 중…