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

HRID 79388

反応式

HRID 79388 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: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

参加物

5

反応物 2

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

生成物 1

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

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-((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).

後処理

  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

出典と根拠

ORDレコード
ord-6b42dcc393e94733ab63114fcc4f6fb2
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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