Methylhydrazine → 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate

HRID 1909924노트

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HRID 1909924 반응식
[C:1]([C:3]1[C:8](F)=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)#[N:2].[CH3:26][NH:27][NH2:28]>CCO>[NH2:2][C:1]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]3)[N:27]([CH3:26])[N:28]=1

참가 물질

4

반응물 2

HCID 6061MethylhydrazineHCID 668237921,1-dimethylethyl 5-(2-cyano-3-fluorophenyl)-2,3-dihydro-1H-indole-1-carboxylate

생성물 1

HCID 668240801,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
100 °C

실험 절차

To a suspension of 1,1-dimethylethyl 5-(2-cyano-3-fluorophenyl)-2,3-dihydro-1H-indole-1-carboxylate (1.60 g, 4.73 mmol) in 30 mL of EtOH was added 7 mL of methylhydrazine in one portion. The mixture was heated in an oil bath at 100° C. for 24 h. LCMS showed conversion complete. The mixture was cooled and concentrated in vacuo. The residue was partitioned between DCM (60 mL) and water (30 mL). The organic was dried over Na2SO4, filtered, and concentrated in vacuo to give 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate as a cream-colored foamy solid (1.70 g).

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between DCM (60 mL) and water (30 mL)
  4. dry with materialThe organic was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-aa6d53c9cd6447e9956be7f7c08f4d36
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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