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

HRID 1662291Notes

Reaction equation

HRID 1662291 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 444333047-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineYield 29.2%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
200 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-098078bdf73f46e9a6b1338245cf9ead
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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