Diisopropylethylamine → HCID 86650408, compound

HRID 240106Notes

Reaction equation

HRID 240106 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.[N:53]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:56]=[C:55]([C:63]2[CH:64]=[C:65]([NH2:69])[CH:66]=[CH:67][CH:68]=2)[CH:54]=1>CN(C=O)C>[N:53]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:56]=[C:55]([C:63]2[CH:64]=[C:65]([NH:69][C:24]([C:19]3[C:20](=[O:23])[O:21][C:22]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][C:13]=4[O:12][C:11]([F:10])([F:28])[F:27])=[O:26])[CH:66]=[CH:67][CH:68]=2)[CH:54]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 41343023-(3-Quinolinyl)benzenamineHCID 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 86650408HCID 86650408, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.013 mL, 0.075 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.019 g, 0.068 mmol) and HATU (0.028 g, 0.075 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-quinolin-3-yl-phenylamine (0.015 g, 0.068 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 68% yield: LCMS (ESI) m/z 477 (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-41f4332cadd24c9187070898bf0982b4
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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