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

HRID 1662291ノート

反応式

HRID 1662291 の反応式
[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

参加物

5

反応物 3

HCID 300Chloroacetic AcidHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 178420844HCID 178420844、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 222Ammonia溶媒

反応条件

温度
200 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-098078bdf73f46e9a6b1338245cf9ead
出典データセット
uspto-grants-2011_10
特許番号
US08030478B2

反応ノート

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