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

HRID 483087

반응식

HRID 483087 반응식
[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]

참가 물질

7

반응물 4

HCID 3671IbudilastHCID 6340IodoethaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-844f97a7dfe84ad1b08ff25636f733d4
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04578392

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