Sodium Hydroxide → 4-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid amide

HRID 1066507

Reaktionsgleichung

[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:18])=[O:17])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:11]([O:35][CH3:36])[N:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].[OH-:37].[Na+]>CCO>[CH3:36][O:35][C:11]1[C:12]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[C:13]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)(=[O:18])=[O:17])[N:14]=[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:37])[CH:8]=2)[N:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

0.356 g of 5-methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide, product of example 19, dissolved in EtOH (5 ml) were treated at RT with 2N NaOH (0.7 ml) and the solution was refluxed for 30 minutes until the transformation was complete according to TLC analysis. The reaction mixture was cooled to 0° C., the pH adjusted to pH=1. The crystalline solid was filtered off, washed with water and dried in a high vacuum to provide the desired 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid amide as an off-white solid. ISN mass spectrum, m/e 521.1 (M−1 calculated for C24H22N6O6S: 521).

Aufarbeitung

temperaturethe solution was refluxed for 30 minutes until the transformation
filtrationThe crystalline solid was filtered off
washwashed with water
customdried in a high vacuum

Quellen und Nachweise

ORD-Eintrag: ord-6a59a4ccbc9e4acd91711f37672e953a
Quelldatensatz: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06242601B1

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