Isonicotinic Acid → 3-(3,4-Diethoxyphenyl)-5-pyridin-4-yl-1,2,4-oxadiazole

HRID 41123

Reaktionsgleichung

Reaktionsgleichung von HRID 41123
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([CH:42]=[CH:43][C:44]=1[O:45][CH2:46][CH3:47])/[C:37](=[N:40]/[H])/[NH:38]O)[CH3:32].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([C:37]2[N:40]=[C:1]([C:2]3[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=3)[O:9][N:38]=2)[CH:42]=[CH:43][C:44]=1[O:45][CH2:46][CH3:47])[CH3:32]

Komponenten

7

Edukt 5

HCID 5922Isonicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 178506510HCID 178506510, Verbindung

Produkt 1

HCID 6663593-(3,4-Diethoxyphenyl)-5-pyridin-4-yl-1,2,4-oxadiazoleAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a microwave vial, a stirring solution of isonicotinic acid (200 mg, 1.62 mmol) in DMF was treated with HOBt (319 mg, 2.43 mmol) and EDCI (467 mg, 2.43 mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of (Z)-3,4-diethoxy-N-hydroxybenzimidamide (436 mg, 1.94 mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130° C. for 35 min in the initiator. The reaction was diluted using a saturated solution of NaHCO3 and extracted with EtOAc (80 ml×3). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (95:5) to offer the product in 26% yield (131 mg) as pale brown solid. 1H NMR (300 MHz, CDCl3): δ 8.85 (d, J=5.4 Hz, 2H), 8.02 (d, J=6.0 Hz, 2H), 7.71 (dd, J1=1.8 Hz, J2=8.1 Hz, 1H), 7.62 (d, J=2.1 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 4.19 (q, J=6.9 Hz, 2H), 4.14 (q, J=6.9 Hz, 2H), 1.50 (t, J=3.0 Hz, 3H), 1.46 (t, J=3.3 Hz, 3H); 13C NMR (75 MHz, CDCl3): δ 173.54, 16928, 151.64, 151.07, 148.91, 131.37, 121.48, 121.15, 118.75, 112.74, 111.82, 64.78, 64.59, 14.87, 14.81. MS (EI) m/z: 312 (M+), HRMS (EI) for C17H17N3O3 (M+): calcd 312.1343. found 312.1348.

Aufarbeitung

  1. stirringThe reaction was stirred for additional 30 min at room temperature
  2. additionThe reaction was diluted
  3. extractionextracted with EtOAc (80 ml×3)
  4. dry with materialThe organic phase was dried over Na2SO4 anhydrous
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-adbaf2d1701747b7912272a9811f0ee8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530503B2

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