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

HRID 632463

반응식

HRID 632463 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c792ba2d334042f8bf03c49549f5aa95
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321748B2

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