2,6-Dichlorophenylacetamidine → 4-[2-(2,6-dichloro-benzyl)-3H-imidazol-4-yl]-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

HRID 559504Notes

Reaction equation

HRID 559504 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH2:20][O:21][CH3:22])[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[CH2:31][C:32]([NH2:34])=[NH:33]>CN(C=O)C>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[CH2:31][C:32]1[NH:33][C:3]([C:5]2[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH2:20][O:21][CH3:22])[C:15]3[S:16][CH:17]=[CH:18][N:19]=3)(=[O:13])=[O:12])=[CH:7][CH:6]=2)=[CH:2][N:34]=1

Participants

4

Reactant 2

HCID 5973572,6-DichlorophenylacetamidineHCID 866116974-(2-bromo-acetyl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Product 1

HCID 670014624-[2-(2,6-dichloro-benzyl)-3H-imidazol-4-yl]-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamideYield 4.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-bromo-acetyl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (0.062 mmol) and the free base of 2-(2,6-dichloro-phenyl)-acetamidine (0.062 mmol) in DMF (2 mL) was heated to 80° C. for 2 h. After cooling to room temperature, the reaction mixture was purified by reverse phase chromatography to yield 4-[2-(2,6-dichloro-benzyl)-3H-imidazol-4-yl]-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (0.003 mmol).

Workup

  1. customthe reaction mixture was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-eb107eb7be864854b77364751878671f
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

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