Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate → HCID 178456633, 화합물

HRID 915052

반응식

HRID 915052 반응식
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH:11]([NH:20][C:21](=[O:31])[CH2:22][NH:23]C(=O)OC(C)(C)C)[C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:3])[CH3:2]>Cl.CO.N1C=CC=CC=1>[OH:31][C:21]1[N:20]=[C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:23][CH:22]=1

참가 물질

5

반응물 1

HCID 86600908Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate

생성물 1

HCID 178456633HCID 178456633, 화합물수율 29.1%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 1049Pyridine용매

반응 조건

온도
82.5 °C

실험 절차

A solution of tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate (310 mg) in 10% hydrogen chloride in MeOH (3 ml) was stirred at 20-25° C. for 18 hours and the mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in pyridine (1.5 ml) and heated at 80-85° C. for 10 hours. After evaporation of pyridine, the mixture was dissolved in CHCl3, washed with 1N HCl, sat. aq. NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give syrup. The syrup was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v) to give 6-(6-hydroxy-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone as a solid (65 mg).

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a residue
  3. customAfter evaporation of pyridine
  4. dissolutionthe mixture was dissolved in CHCl3
  5. washwashed with 1N HCl, sat. aq. NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto give syrup
  9. customThe syrup was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v)

출처 및 근거

ORD 기록
ord-6dcc2126a1a142d8914a67b900e8af3f
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265120B2

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