4-tert-Butylcyclohexylamine → N-(4-tert-Butylcyclohexyl)-N'-(7-hydroxynaphthalen-1-yl)urea

HRID 351286

Reaction equation

HRID 351286 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1([O:18][C:19](=O)[NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=3)[CH:24]=[CH:23][CH:22]=2)C=CC=CC=1>CS(C)=O>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([NH:11][C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 793964-tert-ButylcyclohexylamineHCID 20090380(7-Hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester

Product 1

HCID 18435880N-(4-tert-Butylcyclohexyl)-N'-(7-hydroxynaphthalen-1-yl)urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-tert-Butyl-cyclohexylamine (69 mg, 0.44 mmol) and (7-hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester (125 mg, 0.44 mmol) were combined and stirred at ambient temperature in DMSO (3 mL) overnight. The product was purified by directly injecting the crude reaction onto a reverse phase prep-HPLC (90–10% water:acetonitrile gradient). The appropriate fractions were lyophilized to yield 1-(4-tert-Butyl-cyclohexyl)-3-(7-hydroxy-naphthalen-1-yl)-urea

Workup

  1. customThe product was purified
  2. customreaction onto a reverse phase prep-HPLC (90–10% water:acetonitrile gradient)

Sources & evidence

ORD record
ord-75db14825a1f48a6961e36069b97b72c
Source dataset
uspto-grants-2007_02
Patent number
US07183411B2

Linked notes

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