N,N'-Dimethylethylenediamine → HCID 24986171, compound

HRID 642984Notes

Reaction equation

HRID 642984 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N: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.[NH2:23][CH2:24][C:25]([NH:27][CH3:28])=[O:26].Cl.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[NH2:23][CH2:24][C:25]([N:27]([C:19]1[CH:20]=[CH:21][C:16]([N:14]2[CH:15]=[C:11]([CH2:10][NH:9][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:8])[N:12]=[N:13]2)=[CH:17][CH:18]=1)[CH3:28])=[O:26]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 138422022-amino-N-methylacetamide hydrochlorideHCID 576406935-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide

Product 1

HCID 24986171HCID 24986171, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

The mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (100 mg, 0.22 mmol), H-Gly-NHMe.HCl (110 mg, 0.88 mmol), CuI (42 mg, 0.22 mmol), N,N′-dimethylethylenediamine (24 μL, 0.22 mmol), cesium carbonate (440 mg, 1.4 mmol) in 5 mL dioxane in a sealed tube was stirred for 15 hrs at 120° C. The title compound was isolated directly from the reaction mixture using reverse phase prep HPLC. MS found for C17H17ClN6O2S (M+H)+ 405.1, 407.1 (Cl pattern).

Sources & evidence

ORD record
ord-cba69e7a29f549c7aaca344eef179caf
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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