Acetic Anhydride → HCID 11603507, Verbindung

HRID 1432429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432429
[C:1](OC(=O)C)(=[O:3])[CH3:2].[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[N:21]=[C:20]([CH:22]4[CH2:27][CH2:26][N:25](S(CC5C=CC=CC=5)(=O)=O)[CH2:24][CH2:23]4)[NH:19][C:18]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:16][C:11]=2[O:10][CH2:9]1.C(N(C(C)C)CC)(C)C>C1COCC1>[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[N:21]=[C:20]([CH:22]4[CH2:27][CH2:26][N:25]([C:1](=[O:3])[CH3:2])[CH2:24][CH2:23]4)[NH:19][C:18]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:16][C:11]=2[O:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 10345947HCID 10345947, Verbindung

Produkt 1

HCID 11603507HCID 11603507, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Acetic anhydride (0.011 mL, 0.12 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.035 g, 0.10 mmol; prepared as described in Example 11) and diisopropylethylamine (0.021 mL, 0.12 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 18 hours and was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.010 g (26%) of the title compound as a yellow solid. MS (ESP+) m/z 391.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 8.59 (m, 1H), 7.73 (m, 1H), 7.34 (m, 2H), 6.94 (m, 3H), 5.98 (s, 2H), 4.83 (s, 3H), 4.60 (m, 2H), 4.01 (m, 2H), 3.28 (m, 3H), 2.69 (m, 2H).

Aufarbeitung

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC purification
  7. washeluting with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-7905c16672ec49c7ad4c389bf779df4e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612094B2

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