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

HRID 79463노트

반응식

HRID 79463 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[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 6344Dichloromethane용매HCID 19096565Water ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a609097d36f346878efe52a81c1885ee
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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