Ammonium Chloride → 3-cyclopropyl-1-((2-methyloxazol-4-yl)methyl)-1H-indazol-4-amine

HRID 79463ノート

反応式

HRID 79463 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[N:18]=[C:19]([CH3:22])[O:20][CH:21]=3)[N:5]=2)[CH2:3][CH2:2]1.[Cl-].[NH4+]>CCO.O.ClCCl.[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[N:18]=[C:19]([CH3:22])[O:20][CH:21]=3)[N:5]=2)[CH2:2][CH2:3]1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 672613544-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole

生成物 1

HCID 672600223-cyclopropyl-1-((2-methyloxazol-4-yl)methyl)-1H-indazol-4-amine収率 76.8%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 6344Dichloromethane溶媒HCID 19096565Water ethanol溶媒

実験手順

To a suspension of 4-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole (88 mg, 0.295 mmol) in EtOH/H2O (4:1; 2 mL) was added iron powder (0.33 g, 5.9 mmol) and ammonium chloride (15.8 mg, 0.295 mmol). The reaction mixture was heated at reflux for three hours. The reaction mixture was cooled to ambient temperature, diluted with excess dichloromethane, and the resulting suspension was dried over anhydrous sodium sulfate. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was dissolved in dichloromethane, passed through a silica plug, eluting with 10% MeOH/DCM, and concentrated to afford the product (60.8 mg) as a yellow oil.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for three hours
  3. dry with materialthe resulting suspension was dried over anhydrous sodium sulfate
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in dichloromethane
  7. washeluting with 10% MeOH/DCM
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a609097d36f346878efe52a81c1885ee
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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