Benzyl isocyanate → N'-Benzyl-N-[[4-[[(2-pyridinylmethyl) amino]methyl]phenyl]methyl]-N-(5,6,7,8-tetrahydro-8-quinolinyl)-urea

HRID 1866058Notes

Reaction equation

HRID 1866058 reaction equation
[N+](C1C=CC=CC=1S([N:13]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1)(=O)=O)([O-])=O.[CH2:40]([N:47]=[C:48]=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[CH2:40]([NH:47][C:48](=[O:49])[N:22]([CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[CH:16][CH:17]=1)[CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 22018658N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22708794N'-Benzyl-N-[[4-[[(2-pyridinylmethyl) amino]methyl]phenyl]methyl]-N-(5,6,7,8-tetrahydro-8-quinolinyl)-ureaYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-[5,6,7,8-tetrahydro-8-quinolinyl]-1,4-benzenedimethanamine (140 mg, 0.257 mmol) in dichloromethane (5 ml) cooled to 0° C. was added dropwise, benzyl isocyanate (0.035 mL, 0.284 mmol). The reaction mixture was then allowed to stir at room temperature for two hours. The mixture was evaporated and the residue was purified by column chromatography on silica gel (3% methanol in dichloromethane as eluent) to afford the desired urea in an 81% yield.

Workup

  1. additionwas added dropwise
  2. customThe mixture was evaporated
  3. customthe residue was purified by column chromatography on silica gel (3% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-bd1cdd24c3ba41ab968aa44d650ebc05
Source dataset
uspto-grants-2009_12
Patent number
US07629337B2

Reaction notes

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