Diisopropylethylamine → HCID 86650454, compound

HRID 240176Notes

Reaction equation

HRID 240176 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[O:19][C:18](=[O:21])[C:17]([C:22]([OH:24])=O)=[CH:16]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:49]=[C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[C:57]([C:60]3[CH:61]=[C:62]([NH2:66])[CH:63]=[CH:64][CH:65]=3)[CH:58]=2)[O:53][CH:52]=[CH:51]1>CN(C=O)C>[O:49]=[C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[C:57]([C:60]3[CH:61]=[C:62]([NH:66][C:22]([C:17]4[C:18](=[O:21])[O:19][C:20]5[C:15]([CH:16]=4)=[CH:14][CH:13]=[CH:12][C:11]=5[OH:10])=[O:24])[CH:63]=[CH:64][CH:65]=3)[CH:58]=2)[O:53][CH:52]=[CH:51]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 72457168-Hydroxy-3-carboxy-coumarinHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66864920HCID 66864920, compound

Product 1

HCID 86650454HCID 86650454, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.012 mL, 0.071 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.013 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-(4-oxo-4H-chromen-6-yl)-phenylamine (0.015 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 0.007 g of product in 27% 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-c39c8fad15dd4e0981f863cecbc26b9b
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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