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

Reaction equation

HRID 512567 reaction equation
[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]

Participants

7

Reactant 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

Product 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}acetamideYield 781.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bb73fcd2d0154c4ab16d1a6f074696f8
Source dataset
uspto-grants-2015_08
Patent number
US09102638B2

Linked notes

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