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

反応式

HRID 512566 の反応式
[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

参加物

7

反応物 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

生成物 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収率 802%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-d417c5f001554fca95dba4525fa98a2b
出典データセット
uspto-grants-2015_08
特許番号
US09102638B2

関連ノート

読み込み中…