Amino-6-ethoxybenzothiazole, 2- → N1-(6-ethoxy-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetamide

HRID 512567

반응식

HRID 512567 반응식
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1)[CH3:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:35][O:36][C:37]1[CH:47]=[CH:46][C:45](/[CH:48]=[CH:49]/[C:50](=[O:63])[C:51]2[CH:56]=[C:55]([O:57][CH3:58])[C:54]([O:59][CH3:60])=[C:53]([O:61][CH3:62])[CH:52]=2)=[CH:44][C:38]=1[O:39][CH2:40][C:41](O)=[O:42]>ClCCl.O>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH:11][C:41](=[O:42])[CH2:40][O:39][C:38]3[CH:44]=[C:45](/[CH:48]=[CH:49]/[C:50](=[O:63])[C:51]4[CH:52]=[C:53]([O:61][CH3:62])[C:54]([O:59][CH3:60])=[C:55]([O:57][CH3:58])[CH:56]=4)[CH:46]=[CH:47][C:37]=3[O:36][CH3:35])[S:10][C:6]=2[CH:5]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 7192Amino-6-ethoxybenzothiazole, 2-HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 569681902-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetic acid

생성물 1

HCID 60151528N1-(6-ethoxy-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetamide수율 781.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-ethoxy-2-aminobenzothiazole (194 mg, 1.0 mmol) in dichloromethane (20 mL) was added 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1-hydroxy-1,2,3-benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetic acid (2) (402 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25° C. for 24 h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (9h) (452 mg, 80% yield).

후처리

  1. extractionextracted with dichloromethane
  2. customThe solvent was evaporated under vacuum
  3. customto afford the crude product
  4. customThis was further purified by column chromatography

출처 및 근거

ORD 기록
ord-bb73fcd2d0154c4ab16d1a6f074696f8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102638B2

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