Boron Trichloride → HCID 69211615, Verbindung

Reaktionsgleichung

C([O:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)[CH2:25][CH2:24]2)=[N:12][N:11]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl>[OH:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)[CH2:25][CH2:24]2)=[N:12][N:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 120 mg of 4-benzyloxymethyl-7-methoxy-N-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]phthalazin-1-amine in 4 mL of dichloromethane is stirred under nitrogen at 0° C., followed by dropwise addition of 2.3 mL of a molar solution of boron trichloride in dichloromethane. The reaction medium is stirred for 1 hour at 0° C. and then for 30 minutes at room temperature. It is hydrolysed with aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase is washed with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue is purified on a column of silica (eluent: 100/0 to 85/15 v/v dichloromethane/methanol). 58 mg of product are obtained in the form of a beige-coloured powder.

Aufarbeitung

waitfor 30 minutes at room temperature
extractionextracted with dichloromethane
washThe organic phase is washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue is purified on a column of silica (eluent: 100/0 to 85/15 v/v dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag: ord-191cd4dbd06c46a684baff88706f32a3
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423030B2

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