Diisopropylethylamine → HCID 71212232, Verbindung

HRID 1752259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752259
Cl[C:2]1[N:7]=[N:6][CH:5]=[C:4]2[O:8][CH2:9][CH2:10][CH2:11][C:3]=12.C(N(CC)C(C)C)(C)C.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH2:26]>C(O)(C)C>[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH:26][C:2]1[N:7]=[N:6][CH:5]=[C:4]2[O:8][CH2:9][CH2:10][CH2:11][C:3]=12

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5972502,4-Dimethoxybenzylamine2×HCID 89375780HCID 89375780, Verbindung

Produkt 1

HCID 71212232HCID 71212232, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A mixture of 5-chloro-3,4-dihydro-2H-pyrano[2,3-d]pyridazine (150 mg, 0.879 mmol), N,N-diisopropylethylamine (0.154 mL, 114 mg, 0.879 mmol), and 2,4-dimethoxybenzylamine (294 mg, 1.76 mmol) in isopropanol (2 mL) was heated in a sealed tube 18 hours at 115° C. and then 4.5 hours at 145° C. before addition of excess 2,4-dimethoxybenzylamine (about 2 g, 12 mmol). The reaction was stirred at 145° C. for 18 hours. After cooling to room temperature, isopropanol was removed in vacuo. The crude was then treated with diethyl ether (30 mL). A tan solid was removed by filtration. The filtrate was washed twice with small amounts of saturated aqueous ammonium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated down. The crude was purified by silica gel chromatography with a 0 to 10% methanol/dichloromethane gradient to afford the title compound (159 mg) as an amber foamy oil. MS (ESI) [m/e, (M)+]=301.8. 1H NMR (400 MHz, chloroform-d) δ ppm 8.22 (s, 1H), 7.35 (d, J=8.08 Hz, 1H), 6.36-6.56 (m, 2H), 4.73 (d, J=5.56 Hz, 2H), 4.37-4.56 (m, 1H), 4.11-4.24 (m, 2H), 3.86 (s, 3H), 3.81 (s, 3H), 2.27-2.31 (m, 2H), 2.04-2.11 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customisopropanol was removed in vacuo
  3. additionThe crude was then treated with diethyl ether (30 mL)
  4. customA tan solid was removed by filtration
  5. washThe filtrate was washed twice with small amounts of saturated aqueous ammonium chloride
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. customThe crude was purified by silica gel chromatography with a 0 to 10% methanol/dichloromethane gradient

Quellen und Nachweise

ORD-Eintrag
ord-752e5d075fc04e17ad8180f715d21a13
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163003B2

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