Diisopropylethylamine → HCID 86650455, compound

HRID 240177Notes

Reaction equation

HRID 240177 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[C:60]2[C:55](=[CH:56][CH:57]=[C:58]([C:61]3[CH:62]=[C:63]([NH2:67])[CH:64]=[CH:65][CH:66]=3)[CH:59]=2)[O:54][CH:53]=[CH:52]1>CN(C=O)C>[O:50]=[C:51]1[C:60]2[C:55](=[CH:56][CH:57]=[C:58]([C:61]3[CH:62]=[C:63]([NH:67][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:64]=[CH:65][CH:66]=3)[CH:59]=2)[O:54][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 66864920HCID 66864920, compound

Product 1

HCID 86650455HCID 86650455, compoundYield 100%

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-(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 0.028 g of product in 100% yield: LCMS (ESI) m/z 440 (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-89c5fbc44e2d4bd1a2e8e13b908b4213
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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