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

HRID 2356477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356477
[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

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 204265043-Cyclopropylpropan-1-amine HydrochlorideHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Produkt 1

HCID 112368931-(3-Cyclopropylpropyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}ureaAusbeute 8,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

[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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2476f87f6a8140a4b02c04b68060b114
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759348B2

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