Benzenemethanamine, 4-chloro-3-(trifluoromethyl)- → 1-(4-Chloro-3-trifluoromethyl-benzyl)-3-(7-hydroxy-naphthalen-1-yl)-urea

HRID 351285

Reaction equation

HRID 351285 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].C1([O:20][C:21](=O)[NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([OH:33])[CH:31]=3)[CH:26]=[CH:25][CH:24]=2)C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([OH:33])[CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[O:20])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13]

Participants

4

Reactant 2

HCID 485440Benzenemethanamine, 4-chloro-3-(trifluoromethyl)-HCID 20090380(7-Hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester

Product 1

HCID 104757581-(4-Chloro-3-trifluoromethyl-benzyl)-3-(7-hydroxy-naphthalen-1-yl)-ureaYield 77.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Chloro-3-trifluoromethyl-benzylamine (150 mg, 0.71 mmol) and (7-hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester (200 mg, 0.7 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-Chloro-3-trifluoromethyl-benzyl)-3-(7-hydroxy-naphthalen-1-yl)-urea (212.7 mg, 0.54 mmol). MS (MH+) 394.9; 1H NMR (CD3OD) δ 4.41 (s, 2H), 7.09 (dd, 1H, J=2.4 Hz), 7.21–7.26 (m, 2H), 7.46 (d, 1H, J=7.3 Hz), 7.54 (d, 2H, J=1.0 Hz), 7.62 (d, 1H, J=8.2 Hz), 7.71–7.75 (m, 2H). HPLC Rt=4.4 min (90–10% water:acetonitrile gradient, 100% pure).

Workup

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

Sources & evidence

ORD record
ord-442e0fc0d0f647c7aef36c85fd0aa2d3
Source dataset
uspto-grants-2007_02
Patent number
US07183411B2

Linked notes

Loading…