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Methanol → HCID 66558842, Verbindung

HRID 1530577
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530577
C(O[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([O:22][C:23]2[CH:45]=[CH:44][C:26]3[C:27]4[N:31]([CH2:32][CH2:33][O:34][C:25]=3[CH:24]=2)[CH:30]=[C:29]([C:35]2[N:36]([CH:41]([CH3:43])[CH3:42])[N:37]=[C:38]([CH3:40])[N:39]=2)[N:28]=4)[C:18]([F:21])([F:20])[F:19])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.CO.[CH3:48]CN(C(C)C)C(C)C.C(Cl)(=O)C>[Pd].CC(C)=O>[F:21][C:18]([F:19])([F:20])[CH:17]([CH:14]1[CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH3:48])[CH2:12][CH2:13]1)[O:22][C:23]1[CH:45]=[CH:44][C:26]2[C:27]3[N:31]([CH:30]=[C:29]([C:35]4[N:36]([CH:41]([CH3:43])[CH3:42])[N:37]=[C:38]([CH3:40])[N:39]=4)[N:28]=3)[CH2:32][CH2:33][O:34][C:25]=2[CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68313044HCID 68313044, Verbindung

Produkt 1

HCID 66558842HCID 66558842, VerbindungAusbeute 8,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-{2,2,2-trifluoro-1-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]ethyl}piperidine-1-carboxylic acid benzyl ester from Example 5 (210 mg, 0.34 mmol) in a 1:10 mixture MeOH:acetone (11 mL), was added 10% Pd/C (200 mg). The reaction mixture was stirred at RT under a hydrogen atmosphere for 18 h. The suspension was then filtered through a pad of Celite® and to the filtrate fresh 10% Pd/C (200 mg) was added. The reaction mixture was stirred at RT under a hydrogen atmosphere for 48 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The resulting residue was treated with DIPEA (0.79 mL, 4.42 mmol) and acetyl chloride (0.23 mL, 4.08 mmol) and stirred at RT for 18 h. The crude material was purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a 25 min gradient 10-90% 0.1% HCO2H in acetonitrile/water) affording 179 (15 mg, 8%). LCMS: RT 4.23 min [M+H]+ 533.2. 1H NMR (CDCl3, 400 MHz): δ 8.47 (1H, d, J=8.99 Hz), 7.61 (1H, s), 6.80 (1H, dd, J=9.00, 2.62 Hz), 6.64 (1H, d, J=2.49 Hz), 5.92-5.85 (1H, m), 4.78-4.69 (1H, m), 4.50-4.47 (2H, m), 4.46-4.35 (3H, m), 3.93-3.85 (1H, m), 3.16-3.02 (1H, m), 2.64-2.51 (1H, m), 2.42 (3H, s), 2.27-2.15 (1H, m), 2.10 (3H, d, J=2.36 Hz), 2.05-1.93 (1H, m), 1.89-1.75 (1H, m), 1.64-1.44 (8H, m)

Aufarbeitung

  1. filtrationThe suspension was then filtered through a pad of Celite® and to the filtrate fresh 10% Pd/C (200 mg)
  2. additionwas added
  3. stirringThe reaction mixture was stirred at RT under a hydrogen atmosphere for 48 h
  4. filtrationThe suspension was then filtered through a pad of Celite®
  5. concentrationthe filtrate was concentrated in vacuo
  6. stirringstirred at RT for 18 h
  7. customThe crude material was purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a 25 min gradient 10-90% 0.1% HCO2H in acetonitrile/water)

Quellen und Nachweise

ORD-Eintrag
ord-ac657198bf714cd3acbeab0c176f1b99
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090628B2

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