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Triethylamine → 4-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339564
Notes
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Reaction equation

HRID 339564 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.ON1C2C=CC=CC=2N=N1.[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[CH:8]=3)=[CH:12][CH:13]=2)=[O:35])=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 663454-(Methylamino)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline

Product 1

HCID 583420774-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamideYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a stirred solution of 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.10 g, 0.448 mmol), 1-hydroxybenzotriazole (0.06 g, 0.448 mmol), 4-methylaminobenzoic acid (0.068 g, 0.448 mmol) and triethylamine (62 μl, 0.045 g, 0.448 mmol) in dry DMF (5 ml) at 0° C. was added 1-ethyl-3-[3-(dimethylaminopropyl]-carbodiimide hydrochloride (0.086 g, 0.448 mmol) under an atmosphere or argon. After 10 min the cooling bath was removed and the reaction mixture was stirred at room temperature for 4 d. The reaction mixture was then added to water (150 ml) with stirring and the precipitate was collected by filtration. Purification by flash chromatography (25:1 DCM/MeOH) gave the title compound (0.053 g, 33%) as an almost colourless solid.

Workup

  1. customAfter 10 min the cooling bath was removed
  2. additionThe reaction mixture was then added to water (150 ml)
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. customPurification by flash chromatography (25:1 DCM/MeOH)

Sources & evidence

ORD record
ord-7e9a0e0620404989977747eea8dccf69
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895313B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes