1,1'-Carbonyldiimidazole → HCID 58072196, Verbindung

HRID 1407119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1407119
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=[C:3]1[C:18]([OH:20])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:34][O:35][NH:36][CH3:37].CCN(C(C)C)C(C)C>C1COCC1.O>[CH3:34][O:35][N:36]([CH3:37])[C:18]([C:3]1[C:2](=[O:1])[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)[N:4]=1)=[O:20]

Komponenten

7

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 14813091,4-Dihydro-4-oxo-1-[3-(trifluoromethyl)phenyl]-3-pyridazinecarboxylic acid

Produkt 1

HCID 58072196HCID 58072196, VerbindungAusbeute 104,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxylic acid (2.00 g, 7.04 mmol) and CDI (1.26 g, 7.74 mmol) in THF (20 mL) was heated to 40° C. for 2 h. To the solution were added N-methoxymethanamine hydrochloride (1.03 g, 10.6 mmol) and i-Pr2NEt (1.84 mL, 10.6 mmol) at room temperature. The solution was stirred at room temperature for 20 h. The mixture was diluted with water, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 80/20) to yield the crude title compound (2.40 g) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.28 (3H, s), 3.61 (3H, s), 6.67 (1H, d, J=7.9 Hz), 7.77-7.90 (2H, m), 8.00-8.14 (2H, m), 8.99 (1H, d, J=7.9 Hz).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-2342b619cd684402b67c6683dd453ee4
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916566B2

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