Triethylamine → N-[2-(6-Methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl]-1-(4-methoxyphenyl)cyclopropanecarboxamide

HRID 17862

Reaktionsgleichung

Reaktionsgleichung von HRID 17862
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=2.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2([C:36](O)=[O:37])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:22][O:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:23])[N:6]([CH3:24])[C:5]([CH2:4][CH2:3][NH:2][C:36]([C:33]1([C:30]3[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=3)[CH2:35][CH2:34]1)=[O:37])=[C:14]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 684337913-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride

Produkt 1

HCID 11260220N-[2-(6-Methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl]-1-(4-methoxyphenyl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride (70 mg, 0.20 mmol) in 3 mL of dimethylformamide was added 1-(4-methoxyphenyl)cyclopropanecarboxylic acid (0.39 mg, 0.20 mmol), triethylamine (0.085 mL, 0.61 mmol), 1-hydroxybenzotriazole hydrate (37 mg, 0.24 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (47 mg, 0.24 mmol). After three hours, the mixture was partitioned between EtOAc and water, and the organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was triturated with ether-hexane solution to provide the titled product. HRMS (ES) exact mass calculated for C30H30N2O4 (M+H+): 483.2258. Found 483.2279.

Aufarbeitung

  1. customthe mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was triturated with ether-hexane solution

Quellen und Nachweise

ORD-Eintrag
ord-bce604e62e3c4456a88c7ff567e60035
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741322B2

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