Acetonitrile → HCID 71143552, Verbindung

HRID 2363273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363273
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=23)[CH:3]=[N:2]1.[C:23]([CH:25]=[C:26]1[CH2:29][N:28]([C:30]2[CH:41]=[CH:40][C:33]([C:34]([NH:36][CH:37]([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=2)[CH2:27]1)#[N:24].N12CCCN=C1CCCCC2.C(#N)C>>[C:23]([CH2:25][C:26]1([N:1]2[CH:5]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[C:8]4[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=34)[CH:3]=[N:2]2)[CH2:29][N:28]([C:30]2[CH:41]=[CH:40][C:33]([C:34]([NH:36][CH:37]([CH3:38])[CH3:39])=[O:35])=[CH:32][CH:31]=2)[CH2:27]1)#[N:24]

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 574775784-(1H-Pyrazol-4-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridineHCID 71143653HCID 71143653, Verbindung

Produkt 1

HCID 71143552HCID 71143552, VerbindungAusbeute 100,3 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (0.811 g, 2.58 mmol), 4-[3-(cyanomethylene)azetidin-1-yl]-N-isopropylbenzamide (0.625 g, 2.45 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (190 μL, 1.3 mmol) in acetonitrile (8 mL, 200 mmol) was heated at 50° C. for 1 hour. After cooling, the solvent was removed under reduced pressure. The residue was diluted with dichloromethylene, neutralized with 0.5 N HCl aqueous solution to about pH 7. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product (1.40 g, 84.3%), which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=570.3.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with dichloromethylene
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13b29d724f454525bba5348d24b8b78f
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691807B2

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