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

HRID 2223713

Reaction equation

[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

Participants

Conditions

Temperature: 20 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-3925a18c660d4ba7bf8c3fa196ebf96e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375227B2

Linked notes

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