1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)-N-methoxy-N-methylbenzamide

HRID 750316ノート

反応式

HRID 750316 の反応式
[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2].Cl.[CH3:33][O:34][NH:35][CH3:36].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl.C(N(CC)CC)C>[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([N:35]([O:34][CH3:33])[CH3:36])=[O:29])=[CH:25][CH:24]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 691563104-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)benzoic Acid

生成物 1

HCID 865995664-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)-N-methoxy-N-methylbenzamide収率 78.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To a solution of 4-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)benzoic acid (476 mg) in dichloromethane (10 ml) were added O,N-dimethylhydroxylamine hydrochloride (117 mg), 1-hydroxy-1H-benzotriazole (184 mg) and triethylamine (0.21 ml) and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (287 mg) was added at room temperature, and the mixture was stirred at room temperature for 15 hrs. Dichloromethane was added, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and sodium sulfate was added to dry the mixture. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1→1/9) to give the title compound (407 mg, 78%).

後処理

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and sodium sulfate
  2. additionwas added
  3. customto dry the mixture
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1→1/9)

出典と根拠

ORDレコード
ord-2a09ce3ba91d4cd399df3f7552910f11
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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