Diisopropylethylamine → 8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenyl]-amide

HRID 240110Notes

Reaction equation

HRID 240110 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.[O:53]1[C:58]2[CH:59]=[CH:60][C:61]([C:63]3[CH:64]=[C:65]([NH2:69])[CH:66]=[CH:67][CH:68]=3)=[CH:62][C:57]=2[O:56][CH2:55][CH2:54]1>CN(C=O)C>[O:53]1[C:58]2[CH:59]=[CH:60][C:61]([C:63]3[CH:64]=[C:65]([NH:69][C:24]([C:19]4[C:20](=[O:23])[O:21][C:22]5[C:17]([CH:18]=4)=[CH:16][CH:15]=[CH:14][C:13]=5[O:12][C:11]([F:10])([F:28])[F:27])=[O:26])[CH:66]=[CH:67][CH:68]=3)=[CH:62][C:57]=2[O:56][CH2:55][CH2:54]1

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 549122893-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)anilineHCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Product 1

HCID 866504118-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid [3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenyl]-amideYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.013 mL, 0.072 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.020 g, 0.067 mmol) and HATU (0.028 g, 0.072 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenylamine (0.015 g, 0.067 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 67% yield: LCMS (ESI) m/z 484 (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-5756bb8e5e4a45fda4dcd61bacfdd43b
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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