Ibudilast → 2-Isopropyl-3-(1-hydroxy-1-ethyl-2-methylpropyl)pyrazolo[1,5-a]pyridine

HRID 483087

反応式

HRID 483087 の反応式
[Mg].[CH2:2](I)[CH3:3].[CH:5]([C:8]1[C:16]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1)([CH3:7])[CH3:6].[Cl-].[NH4+]>CCOCC.C1C=CC=CC=1>[CH:5]([C:8]1[C:16]([C:17]([OH:21])([CH2:2][CH3:3])[CH:18]([CH3:20])[CH3:19])=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1)([CH3:7])[CH3:6]

参加物

7

反応物 4

HCID 3671IbudilastHCID 6340IodoethaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

生成物 1

HCID 133917112-Isopropyl-3-(1-hydroxy-1-ethyl-2-methylpropyl)pyrazolo[1,5-a]pyridine

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a suspension of 1.32 g of magnesium in 10 ml of dry ether was gradually added a solution of 17 g of ethyl iodide in 15 ml of dry ether with stirring. After the addition was completed, the stirring was continued for an hour at room temperature. To the mixture was gradually added a solution of 2.5 g of 2-isopropyl-3-isobutyrylpyrazolo[1,5-a]pyridine in 10 ml of dry benzene under stirring. The mixture was stirred for an hour at room temperature, treated with 150 ml of aqueous 20% ammonium chloride solution under ice cooling, and extracted with ether. The ether layer was washed with saturated brine, dried over anhydrous sodium sulfate and cencentrated to dryness. The residue was recrystallized from hexane to give 1.5 g (54%) of the desired derivative as pale gray prisms, mp 96°-98° C.

後処理

  1. additionAfter the addition
  2. waitthe stirring was continued for an hour at room temperature
  3. stirringunder stirring
  4. stirringThe mixture was stirred for an hour at room temperature
  5. extractionextracted with ether
  6. washThe ether layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe residue was recrystallized from hexane
  9. customto give 1.5 g (54%) of the desired derivative as pale gray prisms, mp 96°-98° C.

出典と根拠

ORDレコード
ord-844f97a7dfe84ad1b08ff25636f733d4
出典データセット
uspto-grants-1986_03
特許番号
US04578392

関連ノート

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