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

HRID 2268143Notes

Reaction equation

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

Participants

Conditions

Temperature: 88 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-257933ae30d349fead33f3a237caaf5a
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326495B2

Reaction notes

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