N,N'-Dimethylethylenediamine → 5-chloro-N-((1-(4-(4-ethyl-2,3-dioxopiperazin-1-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 1802657Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[CH:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[CH2:23]([N:25]1[CH2:30][CH2:29][NH:28][C:27](=[O:31])[C:26]1=[O:32])[CH3:24].CNCCNC.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O1CCOCC1.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[CH:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:28]4[CH2:29][CH2:30][N:25]([CH2:23][CH3:24])[C:26](=[O:32])[C:27]4=[O:31])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 (70 mg, 0.16 mmol), N-ethylpiperazine-2,3-dione (45 mg, 0.32 mmol), N,N′-dimethylethylenediamine (0.020 mL, 0.19 mmol) and K2CO3 (65 mg, 0.47 mmol) in DMSO (1 mL) and dioxane (1 mL) was degassed with Ar before being charged with CuI (20 mg, 0.10 mmol). The mixture in a sealed tube was heated at 110° C. overnight. The mixture was then purified by HPLC to give the titled compound (10 mg). MS 458.1 and 460.1 (M+H, Cl pattern).

Workup

customwas degassed with Ar
customThe mixture was then purified by HPLC

Sources & evidence

ORD record: ord-dbb2f556993848118dabb0a321ba2ff0
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349873B2

Reaction notes

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