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Diisopropylethylamine → HCID 86650417, Verbindung

HRID 240118
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 240118
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.[NH:53]1[C:61]2[C:56](=[CH:57][C:58]([C:62]3[CH:63]=[C:64]([NH2:68])[CH:65]=[CH:66][CH:67]=3)=[CH:59][CH:60]=2)[CH:55]=[CH:54]1>CN(C=O)C>[NH:53]1[C:61]2[C:56](=[CH:57][C:58]([C:62]3[CH:63]=[C:64]([NH:68][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:65]=[CH:66][CH:67]=3)=[CH:59][CH:60]=2)[CH:55]=[CH:54]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4135989HCID 4135989, VerbindungHCID 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

Produkt 1

HCID 86650417HCID 86650417, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.014 mL, 0.073 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.020 g, 0.066 mmol) and HATU (0.030 g, 0.073 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(1H-Indol-5-yl)-phenylamine (0.015 g, 0.066 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 0.023 g of product in 68% yield: LCMS (ESI) m/z 465 (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-55650da75f744fafbd68f3ce0f07d5f1
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642788B2

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