Water → N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide

HRID 1097317노트

반응식

HRID 1097317 반응식
Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH3:9][NH:10][C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)=[O:12].O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[CH3:9][NH:10][C:11](=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:2]2[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=2)[CH:18]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 199057185-Chloropyridazin-3(2H)-one

생성물 1

HCID 59443494N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 312751,4-Dioxane용매HCID 22728543Water ethylacetate용매

실험 절차

5-Chloro-pyridazin-3-one (1 eq, 5.06 mmol, 660 mg) and 3-(N-Methylaminocarbonyl)phenyl boronic acid (1.1 eq, 5.56 mmol, 996 mg) are dissolved in dioxane (4 ml), water (2 ml) and EtOH (2 ml) and K2CO3 (2 eq, 10.1 mmol, 1.40 g) is added. Pd(PPh3)4 (0.1 eq, 0.5 mmol, 584 mg) is then added and the reaction mixture is heated using microwave radiation at 140° C. for 20 min. The reaction mixture is diluted with EtOAc/H2O and filtered. The organic layer is then separated and the aqueous layer is extracted with EtOAc (2×20 ml). The organic layer is washed with NaHCO3, brine, dried over MgSO4, filtered and evaporated to dryness to yield N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide as a white solid which did not require further purification; [M+H]+=230

후처리

  1. temperaturethe reaction mixture is heated
  2. customat 140° C.
  3. customfor 20 min
  4. filtrationfiltered
  5. customThe organic layer is then separated
  6. extractionthe aqueous layer is extracted with EtOAc (2×20 ml)
  7. washThe organic layer is washed with NaHCO3, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b7135b2aaafb408a8f5091124285cfc5
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143253B2

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