Triethylamine → N-[5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874414

反応式

HRID 1874414 の反応式
[NH2:1][C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:27])=[C:15]([NH:17][C:18]([C:20]4[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[CH:21]=4)=[O:19])[CH:16]=3)=[CH:9][N:4]2[N:3]=1.C(N(CC)CC)C.[CH:36]1([C:39](Cl)=[O:40])[CH2:38][CH2:37]1>O1CCCC1.O>[CH:36]1([C:39]([NH:1][C:2]2[N:28]=[C:5]3[CH:6]=[CH:7][C:8]([O:10][C:11]4[CH:12]=[CH:13][C:14]([CH3:27])=[C:15]([NH:17][C:18]([C:20]5[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[CH:21]=5)=[O:19])[CH:16]=4)=[CH:9][N:4]3[N:3]=2)=[O:40])[CH2:38][CH2:37]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chloride2 回HCID 57749241N-{5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 25127857N-[5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-{5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (158 mg, 0.419 mmol) and triethylamine (63.8 μL, 0.461 mmol) in tetrahydrofuran (5 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (41.9 μL, 0.461 mmol), and the mixture was stirred at room temperature for 1 hr. Cyclopropanecarbonyl chloride (83.8 μL, 0.922 mmol) was further added and the mixture was stirred for 1 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, sodium carbonate (200 mg), methanol (3 mL) and water (100 μL) were added to the residue, and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=50/50→0/100) and recrystallized from ethyl acetate to give the title compound (112 mg, 60%) as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. stirringthe mixture was stirred for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure, sodium carbonate (200 mg), methanol (3 mL) and water (100 μL)
  8. additionwere added to the residue
  9. stirringthe mixture was stirred at 50° C. for 2 hr
  10. additionThe reaction mixture was diluted with water
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed with water and saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltrated
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. customthe residue was purified by column chromatography (hexane/ethyl acetate=50/50→0/100)
  17. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-6c53f92ef6ac4d6a93975c63c060dfca
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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