Ethanol → N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

HRID 1874605ノート

反応式

HRID 1874605 の反応式
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:37])=[C:19]([CH:36]=2)[O:20][C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28]([NH:30]C(=O)OCC)=S)=[N:25][CH:26]=2)=[O:13])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4])#[N:2].C(O)C.Cl.NO.C([N:47](CC)C(C)C)(C)C>CO>[NH2:47][C:28]1[N:27]=[C:24]2[CH:23]=[CH:22][C:21]([O:20][C:19]3[CH:36]=[C:15]([NH:14][C:12](=[O:13])[C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=4)[CH:16]=[CH:17][C:18]=3[CH3:37])=[CH:26][N:25]2[N:30]=1

参加物

6

反応物 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86631986Ethyl ({5-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy]pyridin-2-yl}carbamothioyl)carbamate

生成物 1

HCID 68985382N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide収率 35%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of the above-mentioned crude product, ethyl ({5-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy]pyridin-2-yl}carbamothioyl)carbamate, in methanol (100 mL)/ethanol (100 mL) were added hydroxylamine hydrochloride (5.08 g, 73.1 mmol) and N,N-diisopropylethylamine (15.3 mL, 87.8 mmol), and the mixture was stirred with heating at 60° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, water (100 mL) was added to the residue, and the mixture was extracted with ethyl acetate (200 mL, 50 mL). The combined organic layer was washed with saturated brine (20 mL) and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (NH silica gel, hexane/ethyl acetate=30/70→0/100), and fractions containing the desired product were concentrated under reduced pressure to give the title compound (1.81 g, 35%) as a colorless solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water (100 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (200 mL, 50 mL)
  4. washThe combined organic layer was washed with saturated brine (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by basic silica gel column chromatography (NH silica gel, hexane/ethyl acetate=30/70→0/100), and fractions
  9. additioncontaining the desired product
  10. concentrationwere concentrated under reduced pressure

出典と根拠

ORDレコード
ord-55e1b260f6d347c4afc2f6212086cbe3
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

反応ノート

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