HCID 67439796, compound → HCID 67438660, compound

HRID 1664787Notes

Reaction equation

[O:1]=[C:2]1[CH:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]2)[CH2:6][C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:4][NH:3]1>C(#N)C.[Cu](Cl)Cl>[O:1]=[C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:4][NH:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

Copper(II) chloride (anhydrous; 1.27 g, 9.45 mmol) was added to a solution of benzyl 4-(3-oxo-6-phenyl-2,3,4,5-tetrahydropyridazine-4-yl)piperidine-1-carboxylate (1.85 g, 4.73 mmol) in acetonitrile (16 mL). The reaction mixture was heated to 90° C. After 2 h, the mixture was allowed to cool 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 (1.1 g). MS 390.1 (M+1).

Workup

temperatureto cool 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-ccba5b7b26f94d6ab5903dba6f9476fa
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039460B2

Reaction notes

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