4-Chloro-3-sulfamoylbenzoic acid → 3-(aminosulfonyl)-4-chloro-N-((1R)-1-(3-chlorophenyl)ethyl)benzamide

HRID 1801577ノート

反応式

HRID 1801577 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][C:13]=1[S:21](=[O:24])(=[O:23])[NH2:22].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O>[NH2:22][S:21]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:12]=1[Cl:11])[C:16]([NH:10][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:9])=[O:17])(=[O:24])=[O:23]

参加物

8

反応物 4

HCID 145684-Chloro-3-sulfamoylbenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2507697(R)-1-(3-chlorophenyl)ethanamine

生成物 1

HCID 91647343-(aminosulfonyl)-4-chloro-N-((1R)-1-(3-chlorophenyl)ethyl)benzamide収率 89.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (R)-1-(3-chlorophenyl)ethanamine (0.426 g, 2.74 mmol) and 4-chloro-3-sulfamoylbenzoic acid 37 (0.452 g, 1.92 mmol) in DMF (5 mL) at room temperature was added EDCI (0.439 g, 2.29 mmol) and HOBT (0.368 g, 2.40 mmol). The reaction mixture was stirred at room temperature for 16 h, and diluted with EtOAc and water. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 50% to 80% EtOAc in hexanes) yielded 3-(aminosulfonyl)-4-chloro-N-((1R)-1-(3-chlorophenyl)ethyl)benzamide 38 (0.643 g, 89.8% yield) as a white solid. Mass spectrum: calculated for C15H14Cl2N2O3S 372.0. found 373.1 (M++1).

後処理

  1. washThe organic phase was washed with water (2×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography on silica gel (eluted with 50% to 80% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-bd2cf040e52e4e5498e9cf4fec8f18ba
出典データセット
uspto-grants-2013_01
特許番号
US08349831B2

反応ノート

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