2-Methylpropanehydrazide → 5-Bromo-3-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine

HRID 1053103

反応式

HRID 1053103 の反応式
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12]([NH:17][NH2:18])(=O)[CH:13]([CH3:15])[CH3:14]>O=P(Cl)(Cl)Cl>[Br:11][C:8]1[CH:7]=[C:3]([C:4]2[O:6][C:12]([CH:13]([CH3:15])[CH3:14])=[N:17][N:18]=2)[C:2]([NH2:1])=[N:10][CH:9]=1

参加物

4

反応物 2

HCID 192392-MethylpropanehydrazideHCID 7374452-Amino-5-bromonicotinic acid

生成物 1

HCID 902732895-Bromo-3-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-amino-5-bromo-nicotinic acid (1.0 g, 4.60 mmol) in POCl3 (20 mL) was added isobutyric acid hydrazide (705 mg, 6.912 mmol) at RT. The reaction temperature was slowly heated to 100° C. and stirred for 18 h. The solvent was evaporated under reduced pressure, the residue was basified with saturated cold sodium bicarbonate solution (50 mL), extracted with ethyl acetate (3×50 mL), organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 100-200 mesh silica gel. The column was eluted with 40% EtOAc in petroleum ether to afford the title compound as a yellow solid.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (3×50 mL), organic layer
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCrude compound was purified by column chromatography
  7. washThe column was eluted with 40% EtOAc in petroleum ether

出典と根拠

ORDレコード
ord-f562512f9ab34561af7c35251160b322
出典データセット
uspto-grants-2016_07
特許番号
US09393248B1

関連ノート

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