Hydrochloric Acid → HCID 136252345, Verbindung

HRID 624547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624547
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:7]=3[N:6]=[C:5]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[C:4]=2[CH:3]=1.Cl>CO.[Pd]>[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][C:14]([CH2:16][NH2:17])=[CH:15][C:7]=3[N:6]=[C:5]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 136377200HCID 136377200, Verbindung

Produkt 1

HCID 136252345HCID 136252345, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-Methyl-10-(4-methyl-piperazin-1-yl)-4H-3-thia-4,9-diaza-benzo[f]azulene-7-carbonitrile, prepared as described in the previous step, (0.25 g) in methanol (90 mL) was added concentrated HCl (0.4 mL) and Pd black (57 mg). Hydrogenation was carried out at 50 psi for 1 h. More Pd black (147 mg) was added. The mixture was shaken at 50 psi for 22 h. The catalyst was filtered and washed with methanol. The filtrate was concentrated, treated with saturated sodium bicarbonate solution (5 mL), and concentrated to dryness. The product was purified by silica column. LC-MS: m/z 342 (M+1). 1H NMR (CD3OD, 400 MHz): δ (ppm) 6.89-6.85 (m, 2H), 6.64 (d, 1H), 6.34 (d, 1H), 3.66 (s, 2H), 3.46 (m, 4H), 2.54 (m, 4H), 2.34 (s, 3H), 2.30 (d, 3H).

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. additiontreated with saturated sodium bicarbonate solution (5 mL)
  5. concentrationconcentrated to dryness
  6. customThe product was purified by silica column

Quellen und Nachweise

ORD-Eintrag
ord-0837dbc0021749d79fd1236cf839205e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303041B2

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