Water → 4-(dimethylamino)-3,5-difluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339567Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([F:28])[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.[CH3:30][NH:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:30][N:31]([CH3:32])[C:26]1[C:25]([F:28])=[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: 120 °C

Procedure

A stirred mixture of 3,4,5-trifluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide (0.10 g, 0.26 mmol), dimethylamine hydrochloride (0.087 g, 1.07 mmol) and potassium carbonate (0.147 g, 1.07 mmol) in dry DMSO (3 ml) was heated at 120° C. for 22.5 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 (40 ml). The solid was dried in an oven at 95° C., and then purified by flash chromatography (25:1 DCM/MeOH) to give the title compound (0.084 g, 80%) as a colourless solid.

Workup

temperatureAfter cooling to room temperature
filtrationthe precipitate was collected by vacuum filtration
washwashed with water (40 ml)
customThe solid was dried in an oven at 95° C.
custompurified by flash chromatography (25:1 DCM/MeOH)

Sources & evidence

ORD record: ord-776090a68f574af2b29168c8d60ff7ae
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895313B2

Reaction notes

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