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

HRID 79423

反応式

HRID 79423 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-23a6bef378da49d3a527ffbf1fd547a2
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

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