异氰酸乙酯 → N-{3-[(2-{[(ethylamino)carbonyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874445

反应方程式

HRID 1874445 反应方程式
[NH2:1][C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:9][N:4]2[N:3]=1.[CH2:29]([N:31]=[C:32]=[O:33])[CH3:30]>N1C=CC=CC=1>[CH2:29]([NH:31][C:32]([NH:1][C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:9][N:4]2[N:3]=1)=[O:33])[CH3:30]

参与物

4

反应物 2

HCID 8022异氰酸乙酯HCID 57749338N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

产物 1

HCID 57749266N-{3-[(2-{[(ethylamino)carbonyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide收率 42%

试剂、催化剂与溶剂 1

HCID 1049吡啶溶剂

反应条件

温度
50 °C

实验过程

A mixture of N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (304 mg, 0.805 mmol), ethyl isocyanate (314 μL, 3.98 mmol) and pyridine (10 mL) was stirred at 50° C. for 18 hr. The reaction solution was concentrated under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with saturated aqueous sodium hydrogen carbonate solution 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 (silica gel, hexane/ethyl acetate=100/0→O/100) and recrystallized from ethyl acetate-hexane to give the title compound (151 mg, 42%) as a white solid.

后处理

  1. concentrationThe reaction solution was concentrated under reduced pressure and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and 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=100/0→O/100)
  8. customrecrystallized from ethyl acetate-hexane

来源与证据

ORD记录
ord-a8cb462fe85d404a8921ee3d611d6a6e
来源数据集
uspto-grants-2012_11
专利号
US08304557B2

关联笔记

加载中…