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Diisopropylethylamine → 8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-(Morpholine-4-sulfonyl)-biphenyl-3-yl)-amide

HRID 240126
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 240126
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([S:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([NH2:74])[CH:69]=2)(=[O:61])=[O:60])[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1>CN(C=O)C>[N:53]1([S:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([NH:74][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:69]=2)(=[O:61])=[O:60])[CH2:54][CH2:55][O:56][CH2:57][CH2:58]1
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Komponenten

6

Edukt 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 668647442'-(Morpholine-4-sulfonyl)-biphenyl-3-ylamineHCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Produkt 1

HCID 86650422
8-Trifluoromethoxy-2-oxo-2H-chromene-3-carboxylic acid (2'-(Morpholine-4-sulfonyl)-biphenyl-3-yl)-amide
Ausbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.009 mL, 0.052 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.013 g, 0.047 mmol) and HATU (0.020 g, 0.052 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 2′-(Morpholine-4-sulfonyl)-biphenyl-3-ylamine (0.015 g, 0.047 mmol) was added and allowed to react overnight. DMF was removed under vacuum and the reaction was resuspended in DMSO. The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage) using a solvent gradient of 10-95% ACN/H2O with 0.05% TFA at a flow rate of 20 mL/min. UV absorbance was monitored at 254 nm and the fractions corresponding to the product peak were collected were collected and the solvent removed under vacuum to give 0.014 g of product in 50% yield: LCMS (ESI) m/z 591 (MH+).

Aufarbeitung

  1. customresulted
  2. customto react overnight
  3. customDMF was removed under vacuum
  4. customThe crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage)
  5. customthe fractions corresponding to the product peak were collected
  6. customwere collected
  7. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-40cfe57b22024436bc4f6ea800c97387
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642788B2

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