1,3-Bis-(2-methyl-quinolin-4-yl)urea → 4-Benzyl-1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-piperidine-4-carboxylic acid

HRID 2223738Notes

Reaction equation

HRID 2223738 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1.[CH3:22][C:23]1[CH:32]=[C:31]([NH:33][C:34](NC2C3C(=CC=CC=3)N=C(C)C=2)=[O:35])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1>C1COCC1>[CH2:15]([C:9]1([C:12]([OH:14])=[O:13])[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][NH:3][C:34]([NH:33][C:31]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=[C:23]([CH3:22])[CH:32]=2)=[O:35])[CH2:7][CH2:8]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 179565591,3-Bis-(2-methyl-quinolin-4-yl)ureaHCID 692175151-(2-Amino-ethyl)-4-benzyl-piperidine-4-carboxylic acid dihydrochloride

Product 1

HCID 179564534-Benzyl-1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Amino-ethyl)-4-benzyl-piperidine-4-carboxylic acid dihydrochloride (3.35 g, 10 mmol), 1,3-bis-(2-methyl-quinolin-4-yl)-urea (3.43 g, 10 mmol) and TEA (5 mL, 36 mmol) are suspended in THF (50 mL) and heated at reflux for 48 h. The solvent is evaporated and the residue purified by HPLC to provide the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. customThe solvent is evaporated
  4. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-f403d4cbf08949c49d7a3a02604b60f7
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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