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

HRID 512566
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HRID 512566 반응식
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:33][O:34][C:35]1[CH:45]=[CH:44][C:43](/[CH:46]=[CH:47]/[C:48](=[O:61])[C:49]2[CH:54]=[C:53]([O:55][CH3:56])[C:52]([O:57][CH3:58])=[C:51]([O:59][CH3:60])[CH:50]=2)=[CH:42][C:36]=1[O:37][CH2:38][C:39](O)=[O:40]>ClCCl.O>[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:39](=[O:40])[CH2:38][O:37][C:36]3[CH:42]=[C:43](/[CH:46]=[CH:47]/[C:48](=[O:61])[C:49]4[CH:50]=[C:51]([O:59][CH3:60])[C:52]([O:57][CH3:58])=[C:53]([O:55][CH3:56])[CH:54]=4)[CH:44]=[CH:45][C:35]=3[O:34][CH3:33])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 151322-Amino-4-methylbenzothiazoleHCID 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 60151529N1-(4-methyl-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetamide
수율 802%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-methyl-2-aminobenzothiazole (164 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 (9k) (440 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-d417c5f001554fca95dba4525fa98a2b
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102638B2

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