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

HRID 1097317

反応式

HRID 1097317 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒HCID 22728543Water ethylacetate溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-b7135b2aaafb408a8f5091124285cfc5
出典データセット
uspto-grants-2012_03
特許番号
US08143253B2

関連ノート

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