Chloroacetic Acid → 7-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

HRID 1662291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662291
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][CH:13]=[N:14][C:7]=12.C(O[C@@H:19]1[O:31][C@H:30]([CH2:32][O:33]C(=O)C)[C@@H:25]([O:26]C(=O)C)[C@H:20]1[O:21]C(=O)C)(=O)C.ClCC(O)=O>N>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:19]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:25]([OH:26])[C@H:20]3[OH:21])[CH:13]=[N:14][C:7]=12

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 178420844HCID 178420844, Verbindung

Produkt 1

HCID 444333047-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of Compound 4 (80 mg, 0.4 mmol), tetra-O-acetyl-β-D-ribofuranose (130 mg, 0.4 mmol) and chloroacetic acid (2 mg) was heated at 200° C. for 5 minutes. The resulting dark syrup was treated with methanolic ammonia (40 ml) at room temperature for 18 hours. After the solvent was distilled off under reduced pressure, the residue was diluted with 30% aqueous CH3CN, and the product was purified by reversed-phase HPLC to give Compound 11 (39 mg, 29%, 2 steps).

Aufarbeitung

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with 30% aqueous CH3CN
  3. customthe product was purified by reversed-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-098078bdf73f46e9a6b1338245cf9ead
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030478B2

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