3-Methoxy-1-(4-methoxybenzyl)-4-propionyl-5,6-dihydro-1H-pyridin-2-one → 1-Cyclopentyl-3-ethyl-6-(4-methoxybenzyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one

HRID 2268143노트

반응식

HRID 2268143 반응식
CO[C:3]1[C:4](=[O:22])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:6][CH2:7][C:8]=1[C:9](=O)[CH2:10][CH3:11].Cl.Cl.[CH:25]1([NH:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1>[CH:25]1([N:30]2[C:3]3[C:4](=[O:22])[N:5]([CH2:13][C:14]4[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)[CH2:6][CH2:7][C:8]=3[C:9]([CH2:10][CH3:11])=[N:31]2)[CH2:29][CH2:28][CH2:27][CH2:26]1

참가 물질

4

반응물 2

HCID 111974373-Methoxy-1-(4-methoxybenzyl)-4-propionyl-5,6-dihydro-1H-pyridin-2-oneHCID 18349526Cyclopentylhydrazine dihydrochloride

생성물 1

HCID 98064151-Cyclopentyl-3-ethyl-6-(4-methoxybenzyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
88 °C

실험 절차

3-Methoxy-1-(4-methoxybenzyl)-4-propionyl-5,6-dihydro-1H-pyridin-2-one (14.471 kg, 47.76 moles) was dissolved in tetrahydrofuran (10.5 gal, 39.7 L) in a clean and dry 100 gallon tank. Cyclopentylhydrazine dihydrochloride (7.664 kg, 44.3 moles) was added and the reaction mixture warmed slowly to 88° C. while nitrogen was swept over the reaction to remove methanol, THF, and HCl. The reaction was monitored by HPLC until the conversion was complete which required heating overnight in most cases. The pot reaction product was a thick dark oil. A sample of 1-cyclopentyl-3-ethyl-6-(4-methoxybenzyl)-1,4,5,6-tetrahydropyrazolo[3,4-c]pyridin-7-one was isolated for characterization.

후처리

  1. customdry 100 gallon tank
  2. customwas swept over the reaction
  3. customto remove methanol, THF, and HCl
  4. temperaturerequired heating overnight in most cases

출처 및 근거

ORD 기록
ord-257933ae30d349fead33f3a237caaf5a
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326495B2

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