3-[1-(1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one → HCID 58577717, compound

HRID 1044185Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[C:18]2[C:13](=[CH:14][C:15]([N:19]3[C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]([CH2:28][CH3:29])[C:20]3=[O:30])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1>C1(C)C=CC=CC=1.[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[N:10]1[C:18]2[C:13](=[CH:14][C:15]([N:19]3[C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]([CH2:28][CH3:29])[C:20]3=[O:30])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[1-(1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) and manganese dioxide (439 mg) in toluene (8 mL) was stirred at 100° C. for 5 h, filtered, treated with water and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with AcOEt/Hexane. Crystallization from AcOEt/Hexane gave the title compound (28.0 mg).

Workup

filtrationfiltered
additiontreated with water
extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with AcOEt/Hexane
customCrystallization from AcOEt/Hexane

Sources & evidence

ORD record: ord-cfbd4a9ec5534e7c831017c21e167e1d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563575B2

Reaction notes

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