N,N'-Dimethylethylenediamine → HCID 89691349, compound

HRID 2202856Notes

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]2[N:25]=[C:24]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[N:23]([CH3:31])[C:22]=2[CH:32]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[CH3:28][C:27]([CH3:30])([CH3:29])[CH2:26][C:24]1[N:23]([CH3:31])[C:22]2[CH:32]=[C:18]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][C:10]3=[O:14])[CH:19]=[CH:20][C:21]=2[N:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (78 mg), 6-bromo-2-(2,2-dimethylpropyl)-1-methyl-1H-benzimidazole (100 mg), N,N′-dimethylethylenediamine (31 mg), copper iodide (68 mg), potassium carbonate (147 mg) and DMSO (2 ml) was heated under Ar atmosphere at 150° C. for 2 h. The mixture was partitioned between 14% aqueous NH3 and EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (50 mg) as a white solid.

Workup

customThe mixture was partitioned between 14% aqueous NH3 and EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-7704c4b9d45f40e5a4137f9bc0de44a3
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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