HCID 67439310, compound → Benzyl 4-(6-cyclopropyl-3-oxo-2,3-dihydropyridazin-4-yl)piperidine-1-carboxylate

HRID 1664793Notes

Reaction equation

[CH:1]1([C:4]2[CH2:5][CH:6]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:13][CH2:12]3)[C:7](=[O:10])[NH:8][N:9]=2)[CH2:3][CH2:2]1>C(#N)C.[Cu](Cl)Cl>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:13][CH2:12]3)[C:7](=[O:10])[NH:8][N:9]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

Copper(II) chloride (anhydrous; 101 mg, 0.75 mmol) was added to a solution of benzyl 4-(6-cyclopropyl-3-oxo-2,3,4,5-tetrahydropyridazine-4-yl)piperidine-1-carboxylate (134 mg, 0.38 mmol) in acetonitrile (16 mL). The reaction mixture was heated to 90° C. After 18 h, the mixture was cooled to ambient temperature and concentrated. Dichloromethane was added to the concentrated mixture, followed by hydrochloric acid (1 N in water). The mixture was extracted with dichloromethane (3×) and the combined organic extracts were dried over magnesium sulfate and concentrated. Purification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) gave the title compound (54 mg). MS 354.1 (M+1).

Workup

temperaturethe mixture was cooled to ambient temperature
concentrationconcentrated
additionDichloromethane was added to the concentrated mixture
extractionThe mixture was extracted with dichloromethane (3×)
dry with materialthe combined organic extracts were dried over magnesium sulfate
concentrationconcentrated
customPurification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

Sources & evidence

ORD record: ord-ca7ce683feea4450afe5244e858ed9d3
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039460B2

Reaction notes

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