Dimethylformamide → 2,2-dimethyl-N-[5-[6-(4-methyl-1-piperidyl)imidazo[2,1-f]pyridazin-2-yl]-2-(trifluoromethyl)phenyl]propanamide

HRID 539751Notes

Reaction equation

CN(C=O)C.[CH3:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:20]1[CH:25]=[CH:24][C:23]2=[N:26][C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:42]([F:45])([F:44])[F:43])=[C:33]([NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=3)=[CH:28][N:22]2[N:21]=1>O>[CH3:38][C:37]([CH3:40])([CH3:39])[C:36]([NH:35][C:33]1[CH:34]=[C:29]([C:27]2[N:26]=[C:23]3[N:22]([CH:28]=2)[N:21]=[C:20]([N:10]2[CH2:11][CH2:12][CH:7]([CH3:6])[CH2:8][CH2:9]2)[CH:25]=[CH:24]3)[CH:30]=[CH:31][C:32]=1[C:42]([F:44])([F:43])[F:45])=[O:41]

Participants

Conditions

Temperature: 120 °C

Procedure

An 8 mL vial is charged with DMF (1 mL), 4-methylpiperidine (0.030 g), Cs2CO3 (0.130 g), and N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.0396 g, 0.1 mmol). The mixture is stirred at 120° C. for 16 hr, then diluted with H2O (5 mL) and extracted with Et2O (3 mL×2). Organics are dried and concentrated onto celite, purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (0.020 g, 43% yield). LCMS m/z=460.6 [M+H]+, tR=3.14 min. (compound same as Example 233)

Workup

extractionextracted with Et2O (3 mL×2)
customOrganics are dried
concentrationconcentrated onto celite
custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-fbce0e91417a49079c8c1f745a35a0b2
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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