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

HRID 240024Notes

Reaction equation

HRID 240024 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[C:20]([OH:21])=[C:19]2[C:14]([CH:15]=[C:16]([C:23]([OH:25])=O)[C:17](=[O:22])[O:18]2)=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:50]1[C:51]([C:59]2[CH:60]=[C:61]([NH2:65])[CH:62]=[CH:63][CH:64]=2)=[CH:52][N:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=12>CN(C=O)C>[N:50]1[C:51]([C:59]2[CH:60]=[C:61]([NH:65][C:23]([C:16]3[C:17](=[O:22])[O:18][C:19]4[C:14]([CH:15]=3)=[CH:13][CH:12]=[C:11]([OH:10])[C:20]=4[OH:21])=[O:25])[CH:62]=[CH:63][CH:64]=2)=[CH:52][N:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=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 151737117,8-Dihydroxy-3-carboxy-coumarin

Product 1

HCID 441973807,8-Dihydroxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (43.1 μL, 0.25 mmol) was added to 7,8-dihydroxy-3-carboxy-coumarin (50 mg, 0.23 mmol) and HATU (94.1 mg, 0.25 mmol) in 2 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (47.1 mg, 0.23 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 for final product: LCMS (ESI) m/z 414 (MH+).

Workup

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

Sources & evidence

ORD record
ord-67c3f102993d43da87a4977c3d6a4495
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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