Sodium Hydroxide → 2-((4-Fluorobenzyl)(4-(pyridin-3-yl)benzyl)amino)thiazole-5-carboxylic acid

HRID 624228

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:23]=[CH:22][C:10]([CH2:11][NH:12][C:13]3[S:14][C:15]([C:18]([O:20]C)=[O:19])=[CH:16][N:17]=3)=[CH:9][CH:8]=2)[CH:2]=1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1.[H-].[Na+].[OH-].[Na+]>CN(C)C=O.O>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:12]([CH2:11][C:10]2[CH:22]=[CH:23][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:8][CH:9]=2)[C:13]2[S:14][C:15]([C:18]([OH:20])=[O:19])=[CH:16][N:17]=2)=[CH:27][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

In a 250 mL round-bottomed flask was added methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate (3 g, 9.22 mmol) and 1-(bromomethyl)-4-fluorobenzene (1.264 ml, 10.14 mmol) in dimethylformamide (46.1 ml). The mixture was cooled to 0° C., sodium hydride (0.738 g, 18.44 mmol) was added carefully; and the mixture was warmed to room temperature. After the mixture was stirred for about 30 minutes, it was found to be predominantely carboxylic acid. 1 N NaOH was added to complete the conversion; and a water work up followed by chromatography provided the title compound.

Aufarbeitung

temperatureand the mixture was warmed to room temperature

Quellen und Nachweise

ORD-Eintrag: ord-53f525ae61584350bf78b2bddc95c8d0
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09302989B2

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