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

HRID 1662291노트

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HRID 1662291 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 222Ammonia용매

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온도
200 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-098078bdf73f46e9a6b1338245cf9ead
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030478B2

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