1,1'-Carbonyldiimidazole → 1-(3-Cyclopropylpropyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}urea

HRID 2354708Notes

Reaction equation

HRID 2354708 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.[C:26]([N:33]1[CH:37]=[CH:36]N=C1)(N1C=CN=C1)=[O:27].[CH:38]1([CH2:41]CCN)[CH2:40][CH2:39]1>ClCCl>[CH:38]1([CH2:41][CH2:36][CH2:37][NH:33][C:26]([NH:1][C:2]2[N:7]=[N:6][C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14](=[O:15])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13]3)=[CH:4][CH:3]=2)=[O:27])[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 204265045648-88-4HCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 112368931-(3-Cyclopropylpropyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}ureaYield 8.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone (200 mg, 0.57 mmol) was slowly added to an ice cold solution of 1,1′-carbonyldiimidazole (110 mg, 0.683 mmol) in anhydrous dichloromethane (15 mL). The temperature was then raised to ambient temperature and the reaction mixture was stirred for another 4 hours. 3-Cyclopropylpropylamine (48.5 mg, 0.569 mmol) was then added to the reaction mixture which was stirred at ambient temperature overnight under nitrogen. The reaction mixture was washed by saturated sodium bicarbonate and brine solution, concentrated and purified by flash column chromatography to yield the product as a white solid (23 mg, 8.5% yield). 1H NMR (300 MHz, CDCl3) δ 10.2, 7.68-7.83, 7.72, 7.65, 7.63, 7.55, 7.36, 7.04, 3.95-4.02, 3.83-3.95, 3.50-3.68, 3.40-3.50, 3.26-3.38, 1.60-1.72, 1.17-1.30, 0.71-0.80, 0.44-0.50, −0.06-0.013. MS (ES+) m/z 477 (M+1).

Workup

  1. stirringwas stirred at ambient temperature overnight under nitrogen
  2. washThe reaction mixture was washed by saturated sodium bicarbonate and brine solution
  3. concentrationconcentrated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-977e739b661343d28f51494b58c823d7
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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