5-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine → HCID 14391767, compound

HRID 868504Notes

Reaction equation

HRID 868504 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[CH:9]=[N:10][C:5]2=[C:4]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:3]=1>O.[Pd]>[NH:20]([C:4]1[CH:3]=[CH:2][N:7]=[C:6]2[N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[CH:9]=[N:10][C:5]=12)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 143917825-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 14391767HCID 14391767, compoundYield 13.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 5-chloro-7-anilino-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine (0.104 g, 0.28 mMol) in 150 mL of water containing 0.1 g of 10% palladium on carbon was hydrogenated in a Parr apparatus for 120 h at 45 psi. The catalyst was removed by filtration and washed well with water. The aqueous filtrate was taken to dryness in vacuo and the residue recrystallized from a minimum of boiling water to give 13 mg of 7-anilino-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine as shown by retention time on reversed phase HPLC and the following: UV max (nm) at pH 1, 304; at pH 13, 301; NMR (DMSO-d6): 9.06 δ (s, 1H, NH); 8.43 (s, 1H, H2); 7.97 (d, 1H, J=5.66 Hz, H5); 7.40-7.07 (m, 5H, Phenyl); 6.88 (d, 1H, J=5.83 Hz, H6); 5.97 (d, 1H, J=6.32 Hz H1').

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed well with water
  3. customthe residue recrystallized from a minimum of boiling water

Sources & evidence

ORD record
ord-527df2b7f923456f8faa7250f6644a7b
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

Loading…