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

HRID 1895264노트

반응식

HRID 1895264 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-caffc5e34ede4089bdde9a3571aa5f61
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513251B2

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