N,N'-Dimethylethylenediamine → 5-Chloro-N-((1-(5-(2-oxopyridin-1(2H)-yl)pyridin-2-yl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 643010

Reaction equation

HRID 643010 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[N:10]=[CH:9]2)=[N:6][CH:7]=1.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O1CCOCC1.[Cu]I>[Cl:22][C:19]1[S:18][C:17]([C:15]([NH:14][CH2:13][C:11]2[N:10]=[CH:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([N:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]4=[O:23])=[CH:7][N:6]=3)[CH:12]=2)=[O:16])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 68507465N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamideHCID 178516071HCID 178516071, compound

Product 1

HCID 249872595-Chloro-N-((1-(5-(2-oxopyridin-1(2H)-yl)pyridin-2-yl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamideYield 6.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide (42 mg, 0.11 mmol), 2-hydroxypyridine (40 mg, 0.42 mmol), N,N′-dimethylethylenediamine (0.035 mL, 0.32 mmol) and K2CO3 (52 mg, 0.38 mmol) in DMSO (1 mL) and dioxane (1 mL) was degassed with Argon before being charged with CuI (23 mg, 0.12 mmol). The mixture was heated at 110° C. overnight in a sealed tube. It was then purified by HPLC to give the title compound (3 mg). MS found for C19H14ClN5O2S: 412.2 and 414.2 (M+H, Cl pattern).

Workup

  1. customwas degassed with Argon
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-3de329def22e45adb61ceacb273dc475
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Linked notes

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