Ammonium formate → N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-(3-methylpyrrolidin-3-yl)cyclohexanecarboxamide

HRID 1943031

Reaktionsgleichung

C([N:8]1[CH2:12][CH2:11][C:10]([N:14]([CH2:23][C:24]2[C:25](=[O:35])[N:26]([CH3:34])[C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])([CH3:13])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:34][N:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:33]=[C:24]([CH2:23][N:14]([C:10]2([CH3:13])[CH2:11][CH2:12][NH:8][CH2:9]2)[C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[C:25]1=[O:35]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

N-(1-benzyl-3-methylpyrrolidin-3-yl)-N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]cyclohexanecarboxamide (1750 mg, 3.71 mmol) and ammonium formate (936 mg, 14.84 mmol) were combined in MeOH (37 mL). 10% Pd/C (350 mg, 3.288 mmol) was added as a slurry in MeOH and the reaction heated to 60° C. for 15 hours. The reaction mixture was filtered through a 0.45 um syringe-tip filter and concentrated in vacuo. The resulting material was partitioned between CH2Cl2 and satd. bicarb, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. This material was carried on without further purification. 1.5 g, 106%.

Aufarbeitung

filtrationThe reaction mixture was filtered through a 0.45 um syringe-tip
filtrationfilter
concentrationconcentrated in vacuo
customThe resulting material was partitioned between CH2Cl2 and satd
extractionbicarb, the aqueous portion extracted 3×CH2Cl2
dry with materialthe organic portion dried (Na2SO4)
concentrationthen concentrated in vacuo
customThis material was carried on without further purification

Quellen und Nachweise

ORD-Eintrag: ord-dc30a69e11ac48e99d2a103f30d42961
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08389720B2

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