Diisopropylethylamine → 6-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

HRID 240035

Reaction equation

HRID 240035 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:28])([F:27])[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][C:18](=[O:23])[C:17]([C:24]([OH:26])=O)=[CH:16]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:53]1[C:54]([C:62]2[CH:63]=[C:64]([NH2:68])[CH:65]=[CH:66][CH:67]=2)=[CH:55][N:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=12>CN(C=O)C>[N:53]1[C:54]([C:62]2[CH:63]=[C:64]([NH:68][C:24]([C:17]3[C:18](=[O:23])[O:19][C:20]4[C:15]([CH:16]=3)=[CH:14][C:13]([O:12][C:11]([F:10])([F:28])[F:27])=[CH:22][CH:21]=4)=[O:26])[CH:65]=[CH:66][CH:67]=2)=[CH:55][N:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=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 100618686-(Trifluoromethoxy)-2-oxo-2H-chromene-3-carboxylic acid

Product 1

HCID 441973856-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amideYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (34.9 μL, 0.20 mmol) was added to 6-trifluoromethoxy-3-carboxy-coumarin (50.0 mg, 0.18 mmol) and HATU (76.3 g, 0.20 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 (38.2 mg, 0.18 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 30.5 mg of product in 36% yield: LCMS (ESI) m/z 466 (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-18d13d9d0b4e486d89f2d2dda2ec1f66
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Linked notes

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