N,N'-Dimethylethylenediamine → HCID 89691116, compound

HRID 2202897Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (100 mg), 6-bromo-2-(2,2-difluorocyclopropyl)-1-methyl-1H-benzimidazole (122 mg), potassium carbonate (176 mg), N,N′-dimethylethylenediamine (0.046 ml), copper iodide (81 mg) and DMSO (3 ml) was stirred at 150° C. under Ar atmosphere for 1 h. The mixture was quenched with 28% NH3 solution and the precipitate was collected by filtration. The solid was dissolved in THF, passed through NH silica gel pad and concentrated in vacuo. The precipitate was recrystallized from EtOAc/MeOH to give the title compound (2 mg) as a pale orange solid.

Workup

customThe mixture was quenched with 28% NH3 solution
filtrationthe precipitate was collected by filtration
dissolutionThe solid was dissolved in THF
concentrationconcentrated in vacuo
customThe precipitate was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record: ord-226d1c5e991644a48e11e2392fa0e950
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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