Ammonium Chloride → N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 1874400

반응식

HRID 1874400 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:16]=2)[CH:13]=1)([O-])=O.[Cl-].[NH4+]>CO.[C].[Pd].[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:16]=2)[CH:13]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 57749101N-[6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

생성물 1

HCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide수율 49%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

실험 절차

To a solution of N-[6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (622 mg, 1.84 mmol) in methanol (10 mL) was added palladium carbon (50% water-containing product, 50 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (20 mL), and ammonium chloride (300 mg, 5.61 mmol) and zinc (360 mg, 5.51 mmol) were added. The mixture was stirred under refluxing conditions for 2 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (NH silica gel, ethyl acetate) to give the title compound (275 mg, 49%) as a white solid.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (20 mL)
  4. stirringThe mixture was stirred under refluxing conditions for 2 hr
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography (NH silica gel, ethyl acetate)

출처 및 근거

ORD 기록
ord-f6853152d4af46a5baed801ee4febc82
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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