Diisopropylethylamine → 8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-cyano-biphenyl-3-yl)-amide

HRID 240114Notes

Reaction equation

HRID 240114 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:28])([F:27])[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.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:53]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([NH2:67])[CH:62]=1)#[N:54]>CN(C=O)C>[C:53]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([NH:67][C:24]([C:19]2[C:20](=[O:23])[O:21][C:22]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[O:12][C:11]([F:10])([F:28])[F:27])=[O:26])[CH:62]=1)#[N:54]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 13931123'-Amino-biphenyl-2-carbonitrileHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Product 1

HCID 866504148-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-cyano-biphenyl-3-yl)-amideYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.015 mL, 0.085 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.021 g, 0.077 mmol) and HATU (0.032 g, 0.085 mmol) in 0.45 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 2′-cyano-biphenyl-3-ylamine (0.015 g, 0.077 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 0.022 g of product in 63% yield: LCMS (ESI) m/z 451 (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-8b95ed3783b94076b0b319aa120203e2
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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