Acrylic Acid → HCID 68845447, compound

HRID 1985843Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][NH:6][C:7]1[N:11]([C@@H:12]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]2[OH:14])[C:10]2[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=2[N:8]=1.[C:28]([OH:32])(=[O:31])[CH:29]=[CH2:30].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:28]([CH:29]=[CH:30][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][NH:6][C:7]1[N:11]([C@@H:12]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]2[OH:14])[C:10]2[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=2[N:8]=1)([OH:32])=[O:31]

Participants

Conditions

Temperature: 100 °C

Procedure

2-(3-Bromobenzylamino)-1-(β-D-ribofuranosyl)-1H-benzimidazole (200 mg), acrylic acid (112 mg), palladium acetate (10 mg) and tri-o-tolylphosphine (28 mg) were suspended in acetonitrile (2 mL). To the mixture was added triethylamine (0.3 mL), and the mixture was stirred at 100° C. for 10 hours. The insoluble material was removed by filtration, and the solvent was removed 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=70/30-10/90) to give the title compound (52 mg).

Workup

customThe insoluble material was removed by filtration
customthe solvent was removed 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=70/30-10/90)

Sources & evidence

ORD record: ord-a4efd77340a547239491cf4b0f3be1fb
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547680B2

Reaction notes

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