8-Hydroxyquinoline → HCID 178523070, compound

HRID 643023Notes

Reaction equation

HRID 643023 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.[N:23]1[CH:28]=[CH:27][N:26]=[C:25]([OH:29])[C:24]=1[OH:30].OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[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]([N:26]4[CH:27]=[CH:28][N:23]=[C:24]([OH:30])[C:25]4=[O:29])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 576406935-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamideHCID 178517837HCID 178517837, compound

Product 1

HCID 178523070HCID 178523070, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °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), 2,3-pyrazinediol (74 mg, 0.66 mmol), CuI (21 mg, 0.11 mmol), 8-hydroxyquinoline (16 mg, 0.11 mmol), potassium carbonate (152 mg, 1.1 mmol) in 2 mL DMSO in a sealed tube was stirred for 15 hrs at 130° C. The title compound was isolated directly from the reaction mixture using reverse phase prep HPLC. MS found for C18H13ClN6O3S (M+H)+ 429.1, 431.1 (Cl pattern).

Sources & evidence

ORD record
ord-7ffd7a46c1ae46c69e70166b6173653f
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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