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

HRID 1874400

反応式

HRID 1874400 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f6853152d4af46a5baed801ee4febc82
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

関連ノート

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