Pyridine → N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylphenyl)pivalamide

HRID 539813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539813
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:18][CH3:19])=[C:15]([CH:17]=3)[NH2:16])[N:10]=2)[N:7]=1.C(#N)C.N1C=CC=CC=1.[CH3:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:18][CH3:19])=[C:15]([NH:16][C:31](=[O:32])[C:30]([CH3:35])([CH3:34])[CH3:29])[CH:17]=3)[N:10]=2)[N:7]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 575162295-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline

Produkt 1

HCID 86667863N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylphenyl)pivalamideAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A flask is charged with 5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline (4.00 g, 0.0146 mol), acetonitrile (120 mL) and pyridine (3.54 mL, 0.0438 mol). The mixture is stirred and trimethylacetyl chloride (1.98 mL, 0.0161 mol) is added and the mixture stirred for 16 hr at room temp. When the reaction is complete the mixture is diluted with water (500 mL) and stirred for 1 hour, and solid collected, washed with water (3×50 mL). Crude product is purified by silica gel chromatography (0-50% EtOAc in CH2Cl2) to give the title compound (4.8 g, 92%). LCMS m/z=357.5, 359.4 [M+H]+, tR=2.57 min.

Aufarbeitung

  1. stirringthe mixture stirred for 16 hr at room temp
  2. stirringstirred for 1 hour
  3. customsolid collected
  4. washwashed with water (3×50 mL)
  5. customCrude product is purified by silica gel chromatography (0-50% EtOAc in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b80fc4985621432b8490cb217cb732aa
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871767B2

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