Diisopropylethylamine → HCID 86711444, Verbindung

HRID 1401097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401097
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[CH:3]1.[F:16][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[C:20]([NH:22][NH:23][CH:24]([CH3:26])[CH3:25])=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[F:16][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[C:20]([NH:22][N:23]([CH:24]([CH3:26])[CH3:25])[C:13](=[O:15])/[CH:12]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)=[O:21]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 5965649(E)-3-(1-methyl-1H-indol-3-yl)acrylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86711429HCID 86711429, Verbindung

Produkt 1

HCID 86711444HCID 86711444, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To solution containing (E)-3-(1-methyl-1H-indol-3-yl)acrylic acid (140.0 mg, 0.70 mmol), 3-fluoro-N′-isopropylbenzohydrazide (209.0 mg, 1.05 mmol) and HATU (399.2 mg, 1.05 mmol) dissolved in DMF (3.0 ml), N,N-diisopropylethylamine (DIPEA)(0.18 ml, 1.05 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (30% EtOAc) for refinement and dried so that ivory (E)-3-fluoro-N′-isopropyl-N′-(3-(1-methyl-1H-indol-3-yl)acryloyl)benzohydrazide was obtained (37.0 mg, 13.9%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated through silica gel chromatography (30% EtOAc) for refinement
  6. dry with materialdried so that ivory (E)-3-fluoro-N′-isopropyl-N′-(3-(1-methyl-1H-indol-3-yl)acryloyl)benzohydrazide
  7. customwas obtained (37.0 mg, 13.9%)

Quellen und Nachweise

ORD-Eintrag
ord-e47f7cfb49d14e8186dc4f608e723ca0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906952B2

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