Iodine → 5-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

HRID 868503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868503
II.C(O[C@@H:7]1[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]1[O:9]C(=O)C)(=O)C.[NH:25]([C:32]1[CH:37]=[C:36]([Cl:38])[N:35]=[C:34]2[NH:39][CH:40]=[N:41][C:33]=12)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[NH:25]([C:32]1[CH:37]=[C:36]([Cl:38])[N:35]=[C:34]2[N:39]([C@@H:7]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]3[OH:9])[CH:40]=[N:41][C:33]=12)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 178478243HCID 178478243, Verbindung

Produkt 1

HCID 143917825-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridineAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

After a crystal of iodine was added to an intimate mixture of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5.2 g, 16 mMol) and 7-anilino-5-chloro-3H-imidazo[4,5-b]pyridine (4.0 g, 16 mMol), the mixture was heated in vacuo at 155° C. After 2 hours, the cooled reaction mixture was suspended in methanol and filtered to remove the unreacted heterocycle (2.29 g). The filtrate was taken to dryness in vacuo and treated with an excess of methanol previously saturated with ammonia. Purification by flash chromatography on silica gel (the residue was adsorbed onto silica gel and placed on the top of the column), elution with chloroform/methanol (20:1 v/v), and removal of the solvent gave 1.22 g (3.2 mMol) of 7-anilino-5-chloro-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine; yield 46.8%; m.p. 157°-160° C. UV max (nm) at pH 1, 307 (ε15,700); pH 13, 250 sh (ε9,900), 300 ε19,400); NMR (DMSO-d6): 9.42 d (s, 1H, NH); 8.50 (s, 1H, H2); 7.43-7.12 (m, 5H, Phenyl); 6.71 (s, 1H, H5); 5.93 (d, 1H, J=5.97 Hz, H1').

Aufarbeitung

  1. customthe cooled reaction mixture
  2. filtrationfiltered
  3. customto remove the unreacted heterocycle (2.29 g)
  4. additiontreated with an excess of methanol previously saturated with ammonia
  5. customPurification by flash chromatography on silica gel (the residue
  6. washelution
  7. customwith chloroform/methanol (20:1 v/v), and removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-403ae4446f244ecabba6954fbfa563c9
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04780452

Notizen zur Reaktion

Wird geladen…