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

HRID 240172Notes

Reaction equation

HRID 240172 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.[O:50]=[C:51]1[NH:55][C:54]2[CH:56]=[CH:57][C:58]([C:60]3[CH:61]=[C:62]([NH2:66])[CH:63]=[CH:64][CH:65]=3)=[CH:59][C:53]=2[NH:52]1>CN(C=O)C>[O:50]=[C:51]1[NH:55][C:54]2[CH:56]=[CH:57][C:58]([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:59][C:53]=2[NH: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 66865547HCID 66865547, compound

Product 1

HCID 866504518-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-phenyl]-amideYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.0085 mL, 0.049 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.009 g, 0.044 mmol) and HATU (0.019 g, 0.049 mmol) in 0.3 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-phenylamine (0.009 g, 0.044 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 0.007 g of product in 39% yield: LCMS (ESI) m/z 428 (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-8a9a30f61ed245eea5fe9c81e8033280
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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