Sodium hydride → HCID 178490766, Verbindung

HRID 1913133

Reaktionsgleichung

Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.[H-].[Na+].F[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[CH3:23])[C:19](=[O:24])[N:18]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH:17]=[CH:16]2>CC(N(C)C)=O>[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=2[CH3:23])[C:19](=[O:24])[N:18]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH:17]=[CH:16]3)[CH2:5][CH2:4]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 1.48 g (9.75 mmol) of trans-4-aminocyclohexanol hydrochloride in 20 ml of dimethylacetamide where added 1.95 g (48.77 mmol) of sodium hydride (60%) and the mixture was stirred for 15 minutes. Subsequently 2.90 g (9.75 mmol) of 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one in 30 ml of dimethylacetamide were added and the reaction mixture was heated to 80° C. for 2 days. After cooling the mixture was poured into 300 ml of ice water and the precipitated crude product was purified by chromatography. First the remaining starting material was eluted with ethyl acetate/heptane (2:1) und finally the desired product was eluted by pure methanol giving 1.98 g 6-(trans-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one.

Aufarbeitung

temperatureAfter cooling the mixture
customthe precipitated crude product
customwas purified by chromatography
washwas eluted with ethyl acetate/heptane (2:1) und finally the desired product
washwas eluted by pure methanol giving 1.98 g 6-(trans-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one

Quellen und Nachweise

ORD-Eintrag: ord-d164da1ab9ac42fa81ce475e2166d472
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08609691B2

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