Pyridine → N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874322

反応式

HRID 1874322 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.N1C=CC=CC=1.[CH3:22][N:23]1[C:27]([C:28](Cl)=[O:29])=[CH:26][C:25]([CH3:31])=[N:24]1>O1CCCC1.O>[NH2:12][C:9]1[N:10]=[CH:11][C:6]([O:5][C:4]2[CH:3]=[C:2]([NH:1][C:28]([C:27]3[N:23]([CH3:22])[N:24]=[C:25]([CH3:31])[CH:26]=3)=[O:29])[CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 577491665-(3-Aminophenoxy)pyridin-2-amine

生成物 1

HCID 57749234N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide収率 61.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5-(3-aminophenoxy)pyridin-2-amine (975 mg, 4.85 mmol) and pyridine (410 μL, 5.09 mmol) in tetrahydrofuran (10 mL) was added dropwise with stirring under ice-cooling a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (807 mg, 5.09 mmol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, extracted with ethyl acetate (×3), and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20→40/100) and recrystallized from ethyl acetate-hexane to give the title compound (964 mg, 61%) as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate (×3)
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20→40/100)
  8. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-6d2bdc40125d4c688e4d52cae12fd48c
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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