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

HRID 431640ノート

反応式

HRID 431640 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c1a2f00cd6634f2db97f4d28c6888f51
出典データセット
uspto-grants-2003_12
特許番号
US06660751B1

反応ノート

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