3-(2-(4-((1H-Benzo[D]imidazol-2-YL)(hydroxy)methyl)phenoxy)pyridin-3-YL)cyclopentanol → (1H-Benzo[D]imidazol-2-YL)(4-(3-(3-hydroxycyclopentyl)pyridin-2-yloxy)phenyl)methanone

HRID 1880164Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:30])[C:11]1[CH:29]=[CH:28][C:14]([O:15][C:16]2[C:21]([CH:22]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:13][CH:12]=1>O1CCCC1.ClCCl.[O-2].[O-2].[Mn+4]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]2[C:21]([CH:22]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:28][CH:29]=1)=[O:30]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 3-(2-(4-((1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)phenoxy)pyridin-3-yl)cyclopentanol (780 mg, 1.943 mmol) in tetrahydrofuran (20 mL) and dichloromethane (50 mL) was treated with manganese dioxide (1351 mg, 15.54 mmol). The reaction was stirred at 23° C. under nitrogen. After 3 h, the reaction was filtered through celite, the filter cake washed with tetrahydrofuran (200 mL), the filtrates combined, concentrated in vacuo and purified by silica gel chromatography (eluant: 1-5% methanol/dichloromethane), affording the product as a white solid. MS (ESI, pos. ion) m/z: 400.1 (M+1). IC50 (uM) +++++.

Workup

filtrationthe reaction was filtered through celite
washthe filter cake washed with tetrahydrofuran (200 mL)
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 1-5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-3fc61ccf3a194549afffadb013740a26
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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