3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole → 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazole-4-amine

HRID 79402

반응식

HRID 79402 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[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=3)[N:5]=2)[CH2:3][CH2:2]1>[Pd].C1(C)C=CC=CC=1>[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:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=3)[N:5]=2)[CH2:2][CH2:3]1

참가 물질

4

반응물 1

HCID 672608093-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

생성물 1

HCID 672592723-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazole-4-amine수율 79.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 1140Toluene용매

반응 조건

온도
75 °C

실험 절차

3-Cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (17.0 g, 55.1 mmol) and 10% Pd/C (1.2 g, 0.6 mmol) were added to toluene (170 mL) in an autoclave. The solution was stirred under 40 psi of H2 at 75° C. for 18 hours. The catalyst was removed by filtration through Celite® and the filter cake was rinsed with toluene (34 mL). The filtrate was concentrated to about 35 mL and heptane (85 mL) was added to the filtrate to precipitate the product which was collected by vacuum filtration and dried under vacuum for 18 hours to afford 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (12.2 g).

후처리

  1. customThe catalyst was removed by filtration through Celite®
  2. washthe filter cake was rinsed with toluene (34 mL)
  3. concentrationThe filtrate was concentrated to about 35 mL and heptane (85 mL)
  4. additionwas added to the filtrate
  5. customto precipitate the product which
  6. filtrationwas collected by vacuum filtration
  7. customdried under vacuum for 18 hours

출처 및 근거

ORD 기록
ord-8b1baa9a4c414152956b97c6f6e31739
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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