Diisopropylethylamine → HCID 44197381, compound

HRID 240027Notes

Reaction equation

HRID 240027 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20](=[O:23])[C:19]([C:24]([OH:26])=O)=[CH:18]2)[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:51]1[C:52]([C:60]2[CH:61]=[C:62]([NH2:66])[CH:63]=[CH:64][CH:65]=2)=[CH:53][N:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=12>CN(C=O)C>[N:51]1[C:52]([C:60]2[CH:61]=[C:62]([NH:66][C:24]([C:19]3[C:20](=[O:23])[O:21][C:22]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][C:13]=4[O:12][CH2:10][CH3:11])=[O:26])[CH:63]=[CH:64][CH:65]=2)=[CH:53][N:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)anilineHCID 7025388-ethoxy-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)

Product 1

HCID 44197381HCID 44197381, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (40.9 μL, 0.23 mmol) was added to 8-ethoxy-3-carboxy-coumarin (50.0 mg, 0.21 mmol) and HATU (89.29 mg, 0.23 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 (44.7 mg, 0.21 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 37.4 mg of product in 42% yield: LCMS (ESI) m/z 426 (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-c9ff6706a85042e9a17a44b19dc45e78
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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