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

HRID 2223713Notes

Reaction equation

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

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27798312-(4-Benzylpiperidin-1-yl)ethan-1-amineHCID 13042979N,2-dimethylquinolin-4-amine

Product 1

HCID 179564923-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-1-methyl-1-(2-methyl-quinolin-4-yl)-urea

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-3925a18c660d4ba7bf8c3fa196ebf96e
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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