Diisopropylethylamine → 7,8-Dimethoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

HRID 240033Notes

Reaction equation

HRID 240033 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[C:21]([O:22][CH3:23])=[C:20]2[C:15]([CH:16]=[C:17]([C:25]([OH:27])=O)[C:18](=[O:24])[O:19]2)=[CH:14][CH:13]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:52]1[C:53]([C:61]2[CH:62]=[C:63]([NH2:67])[CH:64]=[CH:65][CH:66]=2)=[CH:54][N:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=12>CN(C=O)C>[N:52]1[C:53]([C:61]2[CH:62]=[C:63]([NH:67][C:25]([C:17]3[C:18](=[O:24])[O:19][C:20]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[C:12]([O:11][CH3:10])[C:21]=4[O:22][CH3:23])=[O:27])[CH:64]=[CH:65][CH:66]=2)=[CH:54][N:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 149549637,8-Dimethoxy-3-carboxy-coumarin

Product 1

HCID 441973847,8-Dimethoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (38.3 μL, 0.22 mmol) was added to 7,8-dimethoxy-3-carboxy-coumarin (500 mg, 0.20 mmol) and HATU (83.6 mg, 0.22 mmol) in 1 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (41.8 mg, 0.20 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 68.7 mg of product in 78% yield: LCMS (ESI) m/z 442 (MH+).

Workup

  1. customresulted
  2. customto react overnight when a solid
  3. customprecipitated out of solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried under suction, and finally dried overnight in vacuo

Sources & evidence

ORD record
ord-6ed4320365b141d0b1ba4f3e2e877de4
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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