Ammonia → 4-(Benzyloxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202886Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:18]=[CH:19][C:20]2[N:24]=[C:23]([CH2:25][CH3:26])[N:22]([CH3:27])[C:21]=2[CH:28]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>[Cu]I.CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH2:25][CH3:26])[N:22]([CH3:27])[C:21]=3[CH:28]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-benzyloxy-2(1H)-pyridone (1 g), 6-bromo-2-ethyl-1-methyl-1H-benzimidazole (1.19 g), N,N′-dimethylethylenediamine (0.530 ml), copper(I) iodide (0.946 g), potassium carbonate (2.06 g) and DMSO (20 ml) was stirred at 150° C. for 2 h. The mixture was added to 28% NH3 solution, and the precipitate was collected. The solid was dissolved in THF, passed through NH silica pad and concentrated in vacuo to give the title compound (986 mg) as a pink solid. A part of the target compound was treated with activated carbon and recrystallized from THF to give 46.1 mg of the title compound as a white solid.

Workup

customthe precipitate was collected
dissolutionThe solid was dissolved in THF
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-553f78b50f3646499ecb137268e2628f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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