Methanol → 1-(4-morpholin-4-ylphenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 1624733노트

반응식

HRID 1624733 반응식
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25]CO[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:8]=1)=O.[C:27]1([NH:33]N)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:35][OH:36]>>[N:20]1([C:17]2[CH:16]=[CH:15][C:14]([N:9]3[CH:10]=[CH:11][C:12](=[O:13])[C:7]([C:5]4[N:33]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:2]=[CH:3][CH:4]=4)=[N:8]3)=[CH:19][CH:18]=2)[CH2:21][CH2:22][O:36][CH2:35][CH2:25]1

참가 물질

4

반응물 3

HCID 887MethanolHCID 7516PhenylhydrazineHCID 667107903-[3-(dimethylamino)prop-2-enoyl]-1-(4-morpholin-4-ylphenyl)pyridazin-4(1H)-one

생성물 1

HCID 580725341-(4-morpholin-4-ylphenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one수율 8%

실험 절차

To a solution of 3-[3-(dimethylamino)prop-2-enoyl]-1-(4-morpholin-4-ylphenyl)pyridazin-4(1H)-one (crude, 1100 mg, 3.11 mmol) in 20 mL of methanol was added phenylhydrazine (504 mg, 4.67 mmol). The mixture was refluxed for 4 h and concentrated. The residue was dissolved in dichloromethane (20 mL), washed with 1N HCl aqueous solution and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 1-(4-morpholin-4-ylphenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (95 mg, 8% for two steps) as a yellow solid.

후처리

  1. temperatureThe mixture was refluxed for 4 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  4. washwashed with 1N HCl aqueous solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-ed64568f3ab3435598257de8ff11fec9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778944B2

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