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

HRID 539748Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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)

Workup

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

Sources & evidence

ORD record: ord-a2826f11a43c4283a9c4e83983b1743b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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