Propanal → HCID 10424901, Verbindung

HRID 1611700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1611700
[CH3:1][CH:2]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([NH2:19])[CH:15]=[CH:14]2)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].C([BH3-])#N.[CH:23](=O)[CH2:24][CH3:25]>CO.C(Cl)CCl>[CH2:23]([NH:19][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[C:9]([O:8][CH:2]([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:10]=[CH:11][CH:12]=2)[N:17]=1)[CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 527PropanalHCID 498716Cyano-borohydrideHCID 10083869HCID 10083869, Verbindung

Produkt 1

HCID 10424901HCID 10424901, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22134543HCID 22134543, VerbindungLösungsmittel

Versuchsvorschrift

To a 4 mL scintillation vial was added a stir bar and the title compound from Example 16 (15.0 mg, 0.058 mmol). To this was added 0.42 mL of a 1:1 MeOH/ClCH2CH2Cl mixture followed by MP-cyanoborohydride resin (84 mg, 3.7 equiv Argonaut Technologies, Inc.) and 40 μL (10 equiv) of propionaldehyde. The reaction vessel was placed in an oil bath that had been preheated to 80° C. and the contents were allowed to stir overnight. Upon cooling to room temperature, the suspension was filtered and the filtrate was evaporated in vacuo. The crude material was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 8.06 (d, 1H), 7.30 (m, 1H), 7.17 (m, 2H), 6.90 (d, 1H), 4.54–4.81 (m, 1H), 3.38 (m, 2H), 2.38 (m, 1H), 1.80 (m, 1H), 1.50 (m, 2H), 1.39 (d, 3H), 1.03 (t, 3H), 0.96 (s, 9H); MS (DCI/NH3) m/z 301 [M+H]+.

Aufarbeitung

  1. additionTo a 4 mL scintillation vial was added a stir bar
  2. customThe reaction vessel was placed in an oil bath
  3. customhad been preheated to 80° C.
  4. filtrationthe suspension was filtered
  5. customthe filtrate was evaporated in vacuo
  6. customThe crude material was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f8d54dcd541b4b0ab9275e5aaf4b6249
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06989392B2

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