Potassium Fluoride → 6,7-Dichloro-2-isopropyl-3-(5-cyclopropylmethylsulfanyl-1,3,4-thiadiazol-2-ylsulfanyl)quinoxaline

HRID 584652Notes

Reaction equation

HRID 584652 reaction equation
Cl[C:2]1[C:11]([CH:12]([CH3:14])[CH3:13])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:16])=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[F-].[K+].[CH:19]1([CH2:22][S:23][C:24]2[S:25][C:26]([SH:29])=[N:27][N:28]=2)[CH2:21][CH2:20]1>CN(C=O)C>[Cl:16][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[Cl:15])[N:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[C:2]([S:29][C:26]1[S:25][C:24]([S:23][CH2:22][CH:19]3[CH2:20][CH2:21]3)=[N:28][N:27]=1)=[N:3]2

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 223410512,6,7-Trichloro-3-isopropylquinoxalineHCID 1785279755-[(Cyclopropylmethyl)thio]-1,3,4-thiadiazole-2-thiol

Product 1

HCID 98462386,7-Dichloro-2-isopropyl-3-(5-cyclopropylmethylsulfanyl-1,3,4-thiadiazol-2-ylsulfanyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6,7-trichloro-3-isopropylquinoxaline (65 mg, 0.23 mmol) in DMF (4 ml) was added potassium fluoride 40% wt on alumina (103 mg, 0.71 mmol) followed by addition of 2-cyclopropylmethylsulfanyl-5-mercapto-1,3,4-thiadiazole (53 mg, 0.26 mmol). The reaction was stirred overnight at room temperature. The product was purified by flash column chromatography using ethyl acetate:hexanes 1:20 affording the title compound.

Workup

  1. customThe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-31a055901efb45e6bd2541e20714d56c
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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