Diisopropylethylamine → 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(1-methyl-1H-indol-5-yl)-phenyl]-amide

HRID 240180Notes

Reaction equation

HRID 240180 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[O:20][C:19](=[O:22])[C:18]([C:23]([OH:25])=O)=[CH:17]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:50][N:51]1[C:59]2[C:54](=[CH:55][C:56]([C:60]3[CH:61]=[C:62]([NH2:66])[CH:63]=[CH:64][CH:65]=3)=[CH:57][CH:58]=2)[CH:53]=[CH:52]1>CN(C=O)C>[CH3:50][N:51]1[C:59]2[C:54](=[CH:55][C:56]([C:60]3[CH:61]=[C:62]([NH:66][C:23]([C:18]4[C:19](=[O:22])[O:20][C:21]5[C:16]([CH:17]=4)=[CH:15][CH:14]=[CH:13][C:12]=5[O:11][CH3:10])=[O:25])[CH:63]=[CH:64][CH:65]=3)=[CH:57][CH:58]=2)[CH:53]=[CH:52]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668660633-(1-methyl-1H-indol-5-yl)-phenylamine

Product 1

HCID 866504578-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(1-methyl-1H-indol-5-yl)-phenyl]-amideYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.012 mL, 0.071 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.014 g, 0.065 mmol) and HATU (0.027 g, 0.071 mmol) in 0.5 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(1-methyl-1H-indol-5-yl)-phenylamine (0.014 g, 0.065 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 0.013 g of product in 46% yield: LCMS (ESI) m/z 425 (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-c4b57a691a84453d811347dfe3aa53b4
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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