Hydrochloric Acid → 2-{5-Methyl-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-6-carboxylic acid tri-hydrochloride

HRID 1986188

Reaktionsgleichung

C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]3[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([NH:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[N:14]=3)[S:10][C:9]=2[CH:31]=1)=[O:4].C1COCC1.[OH-].[Li+].[ClH:39]>CO.O>[ClH:39].[ClH:39].[ClH:39].[CH3:19][C:18]1[C:13]([C:11]2[S:10][C:9]3[CH:31]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]=3[CH:12]=2)=[N:14][C:15]([NH:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)=[N:16][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

2-{5-Methyl-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-6-carboxylic acid methyl ester (1.31 g, 2.98 mmol) is dissolved in methanol (30 mL), THF (30 mL) and water (10 mL) and lithium hydroxide solution (4.6 mL of 2.0 M solution) is added. The solution is heated at 70° C. for 4.5 hours and 5 N HCl (9 mL) is added in one portion while still heating the solution. The solution is cooled to room temperature and the resulting solid is filtered and washed with methanol. The solid is dried at 60° C. in a vacuum oven for 4 hours to give the title compound (1.43 g, 97% yield). ES+(m/z) 426 [M+H].

Aufarbeitung

temperaturewhile still heating the solution
temperatureThe solution is cooled to room temperature
filtrationthe resulting solid is filtered
washwashed with methanol
customThe solid is dried at 60° C. in a vacuum oven for 4 hours

Quellen und Nachweise

ORD-Eintrag: ord-2b16bcd0d7d6427ba05d937de4fc4041
Quelldatensatz: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07547691B2

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