Diisopropylethylamine → HCID 71468455, Verbindung

HRID 1401075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401075
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:2]1.N1C2C(=CC=CC=2)C(C=C[C:26]([OH:28])=[O:27])=C1.[F:29][C:30]1[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=1)[C:33]([NH:35][NH:36][CH:37]([CH3:39])[CH3:38])=[O:34].CN(C(ON1N=NC2[CH:54]=[CH:55][CH:56]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:67](N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[F:29][C:30]1[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=1)[C:33]([NH:35][N:36]([C:12](=[O:14])/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([C:26]([O:28][C:55]([CH3:54])([CH3:56])[CH3:67])=[O:27])[CH:2]=1)[CH:37]([CH3:39])[CH3:38])=[O:34]

Komponenten

7

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 86711428HCID 86711428, VerbindungHCID 86711429HCID 86711429, Verbindung

Produkt 1

HCID 71468455HCID 71468455, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To solution containing 3-(1H-indol-3-yl)-acrylic acid 3-(1H-indol-3-yl)-acrylic acid (200 mg, 0.7 mmol), 3-fluoro-N′-isopropylbenzohydrazide (204.9 mg, 1.04 mmol) and HATU (397.02 mg, 1.04 mmol) dissolved in DMF (7.0 ml), N,N-diisopropylethylamine (DIPEA)(0.1819 ml, 1.04 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 (36% EtOAc) and dried so that ivory (E)-tert-butyl 3-(3-(2-(3-fluorobenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (159.5 mg, 49%).

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 (36% EtOAc)
  6. dry with materialdried so that ivory (E)-tert-butyl 3-(3-(2-(3-fluorobenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate
  7. customwas obtained (159.5 mg, 49%)

Quellen und Nachweise

ORD-Eintrag
ord-6184c2b1158048c8a42f64b37e6c8340
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906952B2

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