3-(p-Tolyl)propionic acid → N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-3-p-tolyl-propionamide

HRID 1037760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037760
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:7]2=[O:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:42][C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][C:51](O)=[O:52])=[CH:45][CH:44]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:16][N:15]([CH3:17])[CH2:14][CH2:13][N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:51](=[O:52])[CH2:50][CH2:49][C:46]2[CH:47]=[CH:48][C:43]([CH3:42])=[CH:44][CH:45]=2)[C:7]1=[O:12]

Komponenten

6

Edukt 4

HCID 739273-(p-Tolyl)propionic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595794535-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one

Produkt 1

HCID 24784833N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-3-p-tolyl-propionamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one (50 mg, 0.2 mmol), HATU (99 mg, 0.26 mmol), 3-(4-methylphenyl)propionic acid (42 mg, 0.26 mmol) and DIPEA (110 mg, 0.86 mmol) were stirred in methylene chloride (3 mL) at room temperature for 16 hours. The mixture was purified via flash chromatography (12 g of silica gel, 0-10% MeOH/CH2Cl2 gradient) gave N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-3-p-tolyl-propionamide as a white solid (31 mg, 0.08 mmol, 40%).

Aufarbeitung

  1. customThe mixture was purified via flash chromatography (12 g of silica gel, 0-10% MeOH/CH2Cl2 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-57b2d5dd8c9e40c2aed88ac63ff33698
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546579B2

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