2-Chloroethyl isocyanate → 1-(2-Chloroethyl)-3-{6-[4-(2-trifluoromethylbenzoyl)-piperazin-1-YL]pyridazin-3-YL}urea

HRID 499148Notes

Reaction equation

HRID 499148 reaction equation
[NH2:1][C:2]1[N:7]=[N: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.[Cl:26][CH2:27][CH2:28][N:29]=[C:30]=[O:31]>C(O)C.ClCCl>[Cl:26][CH2:27][CH2:28][NH:29][C:30]([NH:1][C:2]1[N:7]=[N:6][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:4][CH:3]=1)=[O:31]

Participants

5

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 113400561-(2-Chloroethyl)-3-{6-[4-(2-trifluoromethylbenzoyl)-piperazin-1-YL]pyridazin-3-YL}ureaYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (0.070 g, 0.200 mmol) in a mixture of ethanol and dichloromethane (1:1, 15 mL) was added 2-chloroethylisocyanate (80.0 μL, 0.79 mmol) in one portion. The mixture was then stirred for 10 minutes at room temperature and then concentrated in vacuo. The residue was washed with 5% HCl solution, water and dried. The residue was purified by column chromatography to afford the title compound in 30% yield (0.028 g). 1H NMR (300 MHz, CDCl3) δ 7.98 (b., s, 1H), 7.75 (d, J=7.0 Hz, 1H), 7.64 (t, J=7.0 Hz, 1H), 7.56 (t, J=7.0 Hz, 1H), 7.37 (d, J=7.0 Hz, 1H), 7.12 (d, J=10.0 Hz, 1H), 4.99 (m, 1H), 4.06-3.89 (m, 2H), 3.69-3.59 (m, 6H), 3.56-3.53 (m, 2H), 3.47-3.44 (m, 2H), 3.35-3.33 (m, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residue was washed with 5% HCl solution, water
  3. customdried
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-95725d4cff304ea1bf92abad488f3211
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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