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

HRID 868503노트

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HRID 868503 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 143917825-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine수율 46.8%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
155 °C

실험 절차

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').

후처리

  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

출처 및 근거

ORD 기록
ord-403ae4446f244ecabba6954fbfa563c9
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04780452

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