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

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

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].

Workup

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

Sources & evidence

ORD record: ord-2b16bcd0d7d6427ba05d937de4fc4041
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547691B2

Linked notes

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