Ammonium Chloride → 3-cyclopropyl-1-((5-methyl-1,3,4-thiadiazol-2-yl)methyl)-1H-indazol-4-amine

HRID 79459노트

반응식

HRID 79459 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[S:18][C:19]([CH3:22])=[N:20][N:21]=3)[N:5]=2)[CH2:3][CH2:2]1.CCO.O.[Cl-].[NH4+]>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[S:18][C:19]([CH3:22])=[N:20][N:21]=3)[N:5]=2)[CH2:2][CH2:3]1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 19096565Water ethanolHCID 672590452-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole

생성물 1

HCID 672599493-cyclopropyl-1-((5-methyl-1,3,4-thiadiazol-2-yl)methyl)-1H-indazol-4-amine수율 48.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 2-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole (61.7 mg, 0.196 mmol) in 4:1 EtOH/H2O (2 mL) was added iron powder (0.219 g, 3.91 mmol) and ammonium chloride (10.5 mg, 0.196 mmol). The reaction mixture was heated to 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 under reduced pressure to afford the product (27 mg) as a yellow solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto 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 under reduced pressure

출처 및 근거

ORD 기록
ord-8b269023fbe949298cc573a557b4a31c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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