Iodoethane → HCID 57720231, compound

HRID 1985840Notes

Reaction equation

[OH:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[N:12]([C@@H:13]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]3[OH:15])[C:11]3[CH:22]=[CH:23][CH:24]=[CH:25][C:10]=3[N:9]=2)=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33].C(=O)([O-])[O-].[K+].[K+].[CH2:40](I)[CH3:41]>CN(C)C=O>[CH2:40]([O:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[N:12]([C@@H:13]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]3[OH:15])[C:11]3[CH:22]=[CH:23][CH:24]=[CH:25][C:10]=3[N:9]=2)=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH3:41]

Participants

Conditions

Temperature: 55 °C

Procedure

2-[4-Hydroxy-3-(4-hydroxybutoxy)benzylamino]-1-(β-D-ribofuranosyl)-1H-benzimidazole (30 mg) and potassium carbonate (18 mg) was suspended in N,N-dimethylformamide (0.7 mL). To the mixture was added ethyl iodide (20 μL), and the mixture was stirred at 55° C. for 16 hour. The insoluble material was removed by filtration, and the reaction mixture was concentrated under reduced pressure. 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=90/10-10/90) to give the title compound (13 mg).

Workup

customThe insoluble material was removed by filtration
concentrationthe reaction mixture was concentrated under reduced pressure
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=90/10-10/90)

Sources & evidence

ORD record: ord-bb2f603eac6b4a4690cccc1c4edab1a6
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547680B2

Reaction notes

Loading…