Triethylamine → 2-[3-(4-Benzyloxybutylamino)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985848Notes

Reaction equation

HRID 1985848 reaction equation
Cl[C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1.[CH2:20]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(O)C(C)C>[CH2:20]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH:37][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46942222423-42-3HCID 231439113-(4-Benzyloxybutylamino)benzylamine

Product 1

HCID 577202012-[3-(4-Benzyloxybutylamino)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazoleYield 30.5%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

2-Chloro-1-(β-D-ribofuranosyl)-1H-benzimidazole (0.14 g) and 3-(4-benzyloxybutylamino)benzylamine (0.36 g) were suspended in isobutanol (5 mL). To the mixture was added triethylamine (0.56 mL), and the mixture was refluxed for 16 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90) to give the title compound (0.08 g).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90)

Sources & evidence

ORD record
ord-063d09b08c5a412b82a560e987c1a8fb
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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