Acetonitrile → N-[5-(6-chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539796Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A 20 mL vial is charged with 5-(6-chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)aniline (0.813 g, 2.6 mmol), acetonitrile (14 mL) and pyridine (0.420 mL). The mixture is added trimethylacetyl chloride (0.640 mL, 5.2 mmol) and stirred for 20 min at 80° C. The acetonitrile solution is concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (256 mg, 25% yield). LCMS m/z=397.5 [M+H]+, tR=2.62 min. (compound same as Example 85)

Workup

concentrationThe acetonitrile solution is concentrated onto celite
custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-d101024be81b4c9e8835056d9140e1eb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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