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

HRID 750316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750316
[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]

Komponenten

7

Edukt 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

Produkt 1

HCID 865995664-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)-N-methoxy-N-methylbenzamideAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2a09ce3ba91d4cd399df3f7552910f11
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402595B2

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