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

HRID 240122Notes

Reaction equation

HRID 240122 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.[NH2:53][C:54]1[CH:55]=[C:56]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[NH:66][C:67](=[O:69])[CH3:68])[CH:57]=[CH:58][CH:59]=1>CN(C=O)C>[C:67]([NH:66][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=1[C:56]1[CH:57]=[CH:58][CH:59]=[C:54]([NH:53][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:55]=1)(=[O:69])[CH3:68]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66865485HCID 66865485, compoundHCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Product 1

HCID 866504208-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-acetylamino-biphenyl-3-yl)-amideYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.013 mL, 0.073 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.018 g, 0.066 mmol) and HATU (0.028 g, 0.073 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, N-(3′-Amino-biphenyl-2-yl)-acetamide (0.015 g, 0.066 mmol) was added and allowed to react overnight 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 0.008 g of product in 26% yield: LCMS (ESI) m/z 483 (MH+).

Workup

  1. customresulted
  2. customto react overnight
  3. customto react overnight when a solid
  4. customprecipitated out of solution
  5. filtrationThe resulting precipitate was filtered
  6. customdried under suction, and finally dried overnight in vacuo

Sources & evidence

ORD record
ord-c41481ee60ad4cec8e757f3010cd1ac6
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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