Iodine → 2-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-1,3,4-oxadiazole

HRID 273068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273068
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[CH:29]([NH:31][NH:32][C:33]([C:35]1([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][N:51]3[CH2:55][CH2:54][CH2:53][CH2:52]3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)=[O:34])=O>ClCCl>[N:51]1([CH2:50][CH2:49][CH2:48][O:47][C:44]2[CH:43]=[CH:42][C:41]([C:35]3([C:33]4[O:34][CH:29]=[N:31][N:32]=4)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:46][CH:45]=2)[CH2:55][CH2:54][CH2:53][CH2:52]1

Komponenten

6

Edukt 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 68576159N'-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazide

Produkt 1

HCID 598374412-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-1,3,4-oxadiazoleAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Triphenylphosphine (0.203 g, 0.78 mmol), iodine (0.198 g, 0.78 mmol) and triethylamine (0.217 mL, 1.56 mmol) were dissolved in dichloromethane (5 mL). The mixture was stirred at room temperature for 10 minutes. N′-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazide (0.145 g, 0.39 mmol) in dichloromethane (5 mL) was added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (25 mL). The organic was dried over sodium sulphate, filtered and concentrated in vacuo to provide a yellow oil. This was purified using preparative HPLC on Fraction-Lynx® eluting with water:acetonitrile:trifluoroacetic acid (95:5:0.1) to provide the title compound (0.028 g, 20%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ1.78-1.85 (m, 4H), 2.05 (m, 2H), 2.30 (m, 2H), 2.56-2.60 (m, 4H), 2.60-2.70 (m, 4H), 3.59 (m, 2H), 3.90-4.05 (m, 4H), 6.90 (d, 2H), 7.20 (d, 2H), 8.30 (s, 1H). HRMS ESI+ m/z 358.2117 [MH]+.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. washwashed with water (25 mL)
  3. dry with materialThe organic was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a yellow oil
  7. customThis was purified
  8. washeluting with water:acetonitrile:trifluoroacetic acid (95:5:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-4ecd098a205f4265befba7e8f9325c6a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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