N-bromobutanimide → 5-Bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1749668노트

반응식

HRID 1749668 반응식
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[O:17][C:16]([C:18]2[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][N:23]=2)=[N:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10]>C1COCC1>[Br:1][C:22]1[N:23]=[C:18]([C:16]2[O:17][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[N:14][N:15]=2)[C:19]([NH2:24])=[N:20][CH:21]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 867276543-(5-Tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

생성물 1

HCID 867276555-Bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine수율 90.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-Bromopyrrolidine-2,5-dione (18.57 g, 104.36 mmol) was added portionwise to a solution of 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (20.8 g, 94.87 mmol) in THF (320 mL) and the solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the residue was dissolved in dichloromethane (300 mL), washed with water (2×150 mL), brine, dried over magnesium sulfate and concentrated. The solvent was evaporated and the crude product was purified by flash chromatography on silica gel, eluting with 0 to 10% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 5-bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (25.5 g, 90%) as a beige solid: 1H NMR Spectrum; (CDCl3) 1.52 (9H, s), 8.23 (1H, s); Mass Spectrum [M+H]+=300.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (300 mL)
  3. washwashed with water (2×150 mL), brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe solvent was evaporated
  7. customthe crude product was purified by flash chromatography on silica gel
  8. washeluting with 0 to 10% ethyl acetate in dichloromethane
  9. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-a2a00dff89354347b1e5b420963b914a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156831B2

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