Benzyl isocyanate → 1-Benzyl-3-{5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridin-2-YL}urea

HRID 2357888Notes

Reaction equation

HRID 2357888 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:26]([N:33]=[C:34]=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH2:26]([NH:33][C:34]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:15])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13]2)=[CH:6][N:7]=1)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 67419145[4-(6-Aminopyridin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

Product 1

HCID 114430801-Benzyl-3-{5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridin-2-YL}ureaYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.12 mmol) in dichloromethane (3 mL) was added benzylisocyanate (0.4 mL, 0.3 mmol). After stirring for 66 h, dichloromethane was removed in vacuo and the residue was diluted with ethyl acetate (20 mL). The organic phase was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a pale white solid (14.6 mg, 30% yield). 1H NMR (300 MHz, CDCl3) δ 9.61, 8.78, 7.73, 7.58, 7.25, 6.78, 4.59, 3.95, 3.32, 3.13, 2.94. MS (ES+) m/z 484.0 (M+1).

Workup

  1. customdichloromethane was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate (20 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-f1a41d45e03c4af9bde25ddcfa0f842c
Source dataset
uspto-grants-2010_07
Patent number
US07763618B2

Reaction notes

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