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 2268143ノート

反応式

HRID 2268143 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
88 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-257933ae30d349fead33f3a237caaf5a
出典データセット
uspto-grants-2001_12
特許番号
US06326495B2

反応ノート

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