1,1'-Carbonyldiimidazole → 3-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-1-methyl-1-(2-methyl-quinolin-4-yl)-urea

HRID 2223713

Reaktionsgleichung

[CH:1]1N=[CH:4][N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[CH2:13]([CH:20]1[CH2:25][CH2:24]N(CCN)C[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CNC1C2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[C:33]([CH3:41])[CH:32]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CS(C)=O.O>[CH2:13]([CH:20]1[CH2:21][CH2:12][N:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[N:3]([CH3:4])[C:2]2[C:1]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[C:33]([CH3:41])[CH:32]=2)[CH2:24][CH2:25]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

To a stirred solution of CDI (178 mg, 1.1 mmol) in DMSO (5 mL) is added a solution of 2-(4-benzyl-piperidin-1-yl)-ethylamine (218 mg, 1 mmol) in DMSO (1 mL). The reaction mixture is stirred at 20° C. for 3 h. Methyl-(2-methyl-quinolin-4-yl)-amine (173 mg, 1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at 20° C. for 24 h, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

Aufarbeitung

stirringThe reaction mixture is stirred at 20° C. for 24 h
customThe reaction mixture is evaporated
customthe residue purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-3925a18c660d4ba7bf8c3fa196ebf96e
Quelldatensatz: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07375227B2

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