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

HRID 339567
Notes
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Reaction equation

HRID 339567 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 583420973,4,5-trifluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

Product 1

HCID 451374464-(dimethylamino)-3,5-difluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamideYield 80%

Reagents, catalysts & solvents

1
HCID 679Dimethyl SulfoxideSolvent

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

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with water (40 ml)
  4. customThe solid was dried in an oven at 95° C.
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes