Pyridine → N-{2-[4-(1H-Benzimidazol-2-yl)-piperazin-1-yl]-ethyl}-2,4-dichloro-5,N-dimethyl-benzenesulfonamide

HRID 431640Notes

Reaction equation

HRID 431640 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].Cl.[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][NH:32][CH3:33])[CH2:26][CH2:25]1.N1C=CC=CC=1>ClCCl>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[N:24]1[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][N:32]([CH3:33])[S:10]([C:3]2[CH:4]=[C:5]([CH3:9])[C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])(=[O:12])=[O:11])[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1199142,4-Dichloro-5-methylbenzene-1-sulphonyl chlorideHCID 18761519{2-[4-(1h-Benzimidazol-2-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt

Product 1

HCID 9913117N-{2-[4-(1H-Benzimidazol-2-yl)-piperazin-1-yl]-ethyl}-2,4-dichloro-5,N-dimethyl-benzenesulfonamideYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2,4-dichloro-5-methylbenzenesulphonyl chloride (81 mg, 0.31 mmol), {2-[4-(1H-Benzimidazol-2-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt (D23) (80 mg, 0.31 mmol) and pyridine (0.5 ml) in dry dichloromethane (5 ml) was stirred at room temperature for 17 h. The mixture was then diluted with dichloromethane (30 ml), washed with aqueous sodium bicarbonate (1×10 ml) and dried.(MgSO4). The solvent was evaporated and the residue was co-evaporated with toluene (5 ml). Column chromatography of the residue (eluting with methanol-dichloromethane gradient) gave the product as a yellowish solid (25 mg, 17%); MS: m/z (MH+)=482.

Workup

  1. washwashed with aqueous sodium bicarbonate (1×10 ml)
  2. customdried
  3. customThe solvent was evaporated
  4. washColumn chromatography of the residue (eluting with methanol-dichloromethane gradient)

Sources & evidence

ORD record
ord-c1a2f00cd6634f2db97f4d28c6888f51
Source dataset
uspto-grants-2003_12
Patent number
US06660751B1

Reaction notes

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