Hydrochloric Acid → 3-[({6-Amino-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl}oxy)methyl]benzenecarboxylic acid

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Reaktionsgleichung

CC(C)([O-])C.[K+].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=[CH:13][CH:14]=1.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]([C:33]#[N:34])=[C:21](SC2C=CC=CC=2)[N:20]=1.Cl.C[O:44][CH2:45][CH2:46][O:47]C>O>[NH2:18][C:19]1[N:20]=[C:21]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)[C:22]([C:33]#[N:34])=[C:23]([C:27]2[CH:28]=[CH:29][C:30]([O:44][CH2:45][CH2:46][OH:47])=[CH:31][CH:32]=2)[C:24]=1[C:25]#[N:26]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

4.72 g (42.06 mmol) of potassium tert-butoxide were suspended in 25 ml of 1,2-dimethoxyethane. After addition of 1.73 g (10.51 mmol) of 3-(hydroxymethyl)benzenecarboxylic acid (Example 66A) and 1.72 g (5.26 mmol) of 2-amino-4-phenyl-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile (Example 36A), the mixture was stirred at 60° C. overnight. After cooling of the reaction mixture, 50 ml of water were added. With ice-cooling, the clear solution was acidified to pH 6-7 using conc. hydrochloric acid. The solution was evaporated. Purification was by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 1/1, finally acetonitrile/water 10/1).

Aufarbeitung

additionwere added
temperatureWith ice-cooling
customThe solution was evaporated
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-46a0d27483334464b0612eabc200768e
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09187428B2

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