2-Dimethylaminopyridine → HCID 22281926、化合物

HRID 1368659ノート

反応式

HRID 1368659 の反応式
[C:1]1(/[CH:7]=[CH:8]/[S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[NH2:22][C:23]1[N:27]([CH3:28])[N:26]=[C:25]([O:29][CH2:30][CH2:31][OH:32])[C:24]=1[C:33]1[CH:41]=[CH:40][C:36]2[O:37][CH2:38][O:39][C:35]=2[CH:34]=1>N1C=CC=CC=1>[O:37]1[C:36]2[CH:40]=[CH:41][C:33]([C:24]3[C:25]([O:29][CH2:30][CH2:31][OH:32])=[N:26][N:27]([CH3:28])[C:23]=3[NH:22][S:9](/[CH:8]=[CH:7]/[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:11])=[O:10])=[CH:34][C:35]=2[O:39][CH2:38]1

参加物

5

反応物 3

HCID 218852-DimethylaminopyridineHCID 5369377(E)-2-phenylethene-1-sulfonyl chlorideHCID 22281969HCID 22281969、化合物

生成物 1

HCID 22281926HCID 22281926、化合物収率 80.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

(E)-2-phenylethensulfonyl chloride (381 mg) and dimethylaminopyridine (77 mg) were added at room temperature under an atmosphere of nitrogen to a solution of 2-{[5-amino-4-(1,3-benzodioxol-5-yl)-1-methyl-1H-pyrazol-3-yl]oxy}-1-ethanol (200 mg) (Preparation 45) in anhydrous pyridine (6 ml). After 24 h, the mixture was concentrated under reduced pressure. To the yellow solid was added water (30 ml), an aqueous solution of HCl (1N) to acidify the solution and the mixture was extracted with dichloromethane (3×30 ml). The organic fractions were combined, dried on sodium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (6 ml) and dichloromethane (1 ml) and an excess of an aqueous solution of sodium hydroxyde (2N) was added. The reaction was stirred overnight. The reaction mixture was then diluted with dichloromethane (100 ml), acidified with an aqueous solution of HCl (1N). The phases were separated and the aqueous phase was extracted with dichloromethane (2×50 ml). The combined organic fractions were dried on sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 20 g) eluted with dichloromethane:methanol (95:5) to yield the title compound as colourless solid (257 mg).

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the yellow solid was added water (30 ml)
  3. extractionthe mixture was extracted with dichloromethane (3×30 ml)
  4. customdried on sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethanol (6 ml)
  7. additiondichloromethane (1 ml) and an excess of an aqueous solution of sodium hydroxyde (2N) was added
  8. additionThe reaction mixture was then diluted with dichloromethane (100 ml)
  9. customThe phases were separated
  10. extractionthe aqueous phase was extracted with dichloromethane (2×50 ml)
  11. customThe combined organic fractions were dried on sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by column chromatography (silica, 20 g)
  14. washeluted with dichloromethane:methanol (95:5)

出典と根拠

ORDレコード
ord-9433d526cd5d4f428149211c49480ce6
出典データセット
uspto-grants-2003_06
特許番号
US06573270B1

反応ノート

読み込み中…