1-Hydroxybenzotriazole → 5-(5-(Pyrrol-1-yl)pyridin-3-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

HRID 713761

Reaktionsgleichung

Reaktionsgleichung von HRID 713761
[N:1]1([C:6]2[CH:7]=[N:8][CH:9]=[C:10]([CH:14]=2)[C:11]([OH:13])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.Cl.CNCCCN=C=NCC.ON1C2C=CC=CC=2N=N1.O[N:37]=[C:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=1>CN(C)C=O>[N:1]1([C:6]2[CH:14]=[C:10]([C:11]3[O:13][N:45]=[C:38]([C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)[N:37]=3)[CH:9]=[N:8][CH:7]=2)[CH:2]=[CH:3][CH:4]=[CH:5]1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 308113N-HydroxynicotinimidamideHCID 20501015-(1H-pyrrol-1-yl)pyridine-3-carboxylic acidHCID 9794023N-(3-methylaminopropyl)-N'-ethylcarbodiimide hydrochloride

Produkt 1

HCID 670265495-(5-(Pyrrol-1-yl)pyridin-3-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(1H-pyrrol-1-yl)nicotinic acid (Maybridge, 188 mg, 1.00 mmol) in dimethylformamide (anhydrous, 5 mL) was added N-(3-methylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (Aldrich, 192 mg, 1.00 mmol) and 1-hydroxybenzotriazole (HOBT) hydrate (Fluka, 153 mg, 1.00 mmol). The mixture was stirred at ambient temperature for 20 minutes. N′-Hydroxynicotinimidamide (137 mg, 1.0 mmol) was added and the mixture was stirred for 6-10 hours, and then warmed to 140° C. for 2-4 hours. The reaction was cooled to ambient temperature and triturated with water (10 mL). The precipitate was filtered and dried under vacuum to give the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 6.34-6.44 (m, 2H), 7.60-7.82 (m, 3H), 8.50 (dt, J=8.1, 1.9 Hz, 1H), 8.71 (dd, J=2.5, 1.9 Hz, 1H), 8.84 (dd, J=4.6, 1.5 Hz, 1H), 9.21 (d, J=1.7 Hz, 1H), 9.26 (d, J=2.4 Hz, 1H), 9.31 (d, J=1.7 Hz, 1H) ppm; MS (DCl/NH3) m/z 290 (M+H)+.

Aufarbeitung

  1. stirringthe mixture was stirred for 6-10 hours
  2. temperaturewarmed to 140° C. for 2-4 hours
  3. temperatureThe reaction was cooled to ambient temperature
  4. customtriturated with water (10 mL)
  5. filtrationThe precipitate was filtered
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-efa7c07280ec4be2b8a637eeb73fefcf
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09186407B2

Verknüpfte Notizen

Wird geladen…