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

HRID 539752Notes

Reaction equation

CN(C=O)C.[CH3:6][C@H:7]1[O:12][C@@H:11]([CH3:13])[CH2:10][NH:9][CH2:8]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:21]1[CH:26]=[CH:25][C:24]2=[N:27][C:28]([C:30]3[CH:31]=[CH:32][C:33]([C:43]([F:46])([F:45])[F:44])=[C:34]([NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH:35]=3)=[CH:29][N:23]2[N:22]=1>O>[CH3:13][C@H:11]1[O:12][C@@H:7]([CH3:6])[CH2:8][N:9]([C:21]2[CH:26]=[CH:25][C:24]3=[N:27][C:28]([C:30]4[CH:31]=[CH:32][C:33]([C:43]([F:44])([F:45])[F:46])=[C:34]([NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH:35]=4)=[CH:29][N:23]3[N:22]=2)[CH2:10]1

Participants

Conditions

Temperature: 120 °C

Procedure

An 8 mL vial is charged with DMF (1 mL), cis-2,6-dimethylmorpholine (0.034 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 (0.027 g, 57% yield). LCMS m/z=476.6 [M+H]+, tR=2.77 min. (compound same as Example 250)

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-1345f86b9533409cb984cb1d39e5f053
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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