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

HRID 1801577노트

반응식

HRID 1801577 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bd2cf040e52e4e5498e9cf4fec8f18ba
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349831B2

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