Water → 4-(dimethylamino)-3-fluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339569

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1F)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]3[CH:23]=2)=[CH:10][CH:9]=1)=[O:6].Cl.[CH3:29][NH:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:29][N:30]([CH3:31])[C:26]1[CH:25]=[CH:24][C:4]([C:5]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]4[CH:23]=3)=[CH:12][CH:13]=2)=[O:6])=[CH:3][C:2]=1[F:1]

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred mixture of 3,4-difluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide (0.10 g, 0.275 mmol), dimethylamine hydrochloride (0.045 g, 0.551 mmol) and potassium carbonate (0.080 g, 0.577 mmol) in dry DMSO (3 ml) was heated at 100° C. for 18 h. After cooling to room temperature, the reaction mixture was added to water (100 ml) and the precipitate was collected by vacuum filtration, and washed with water (50 ml). The air-dried solid was then purified by flash chromatography (25:1 DCM/MeOH) to give the title compound (0.066 g, 62%) as a colourless solid.

Workup

temperatureAfter cooling to room temperature
filtrationthe precipitate was collected by vacuum filtration
washwashed with water (50 ml)
customThe air-dried solid was then purified by flash chromatography (25:1 DCM/MeOH)

Sources & evidence

ORD record: ord-21860898a6cf42faa68628315740fb73
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895313B2

Linked notes

Loading…