Acetonitrile → N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamide

HRID 539748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539748
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[C:15]([CH:17]=3)[NH2:16])=[CH:10][N:4]2[N:3]=1.C(#N)C.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:19])([F:20])[F:21])=[C:15]([NH:16][C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[CH:17]=3)[N:8]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 866678495-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)aniline

Produkt 1

HCID 86667850N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamideAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 40 mL vial is charged with 5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)aniline (0.531 g, 1.7 mmol), acetonitrile (14 mL), and pyridine (0.275 mL). The stirred mixture is added trimethylacetyl chloride (0.419 mL, 3.4 mmol) and heated for 20 min at 80° C. The reaction is concentrated, taken into EtOAc (25 mL), washed once with HCl (15 mL, 1M) then NaOH (15 mL, 1M). Organic is dried, concentrated and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (630 mg, 93% yield). LCMS (m/z)=397.4, 399.3 [M+H]+, tR=2.87 min. (compound same as Example 126)

Aufarbeitung

  1. concentrationThe reaction is concentrated
  2. washwashed once with HCl (15 mL, 1M)
  3. customOrganic is dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a2826f11a43c4283a9c4e83983b1743b
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871767B2

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