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

HRID 1986233Notes

Reaction equation

HRID 1986233 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([C:15]3[C:20]([Cl:21])=[CH:19][N:18]=[C:17]([NH:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[N:16]=3)[S:12][C:11]=2[CH:33]=1)=[O:6].C1COCC1.[ClH:39]>CO.O>[ClH:21].[ClH:39].[ClH:21].[Cl:21][C:20]1[C:15]([C:13]2[S:12][C:11]3[CH:33]=[C:7]([C:5]([OH:6])=[O:4])[CH:8]=[CH:9][C:10]=3[CH:14]=2)=[N:16][C:17]([NH:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]2)=[N:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 688569182-{5-Chloro-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-6-carboxylic acid methyl ester

Product 1

HCID 688561812-{5-Chloro-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-6-carboxylic acid tri-hydrochlorideYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous LiOH solution (2.0 M, 2.8 mL) is added to a stirred suspension of 2-{5-chloro-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-6-carboxylic acid methyl ester (0.840 g, 1.80 mmol) in MeOH (20 mL)/THF (20 mL)/H2O (6 mL), the resultant mixture is heated at 70° C. for 4.5 hours. While heating the solution, 5.0 N HCl (3.4 mL) is added in one portion then the solution is allowed to cool to ambient temperature to from a suspension. After filtration, the solid is dried in a vacuum oven at 60° C. for 4 hours to give the title compound (0.64 g, 67% yield). ES+(m/z) 446 (35Cl) and 448 (37Cl) [M+H].

Workup

  1. additionis added in one portion
  2. filtrationAfter filtration
  3. customthe solid is dried in a vacuum oven at 60° C. for 4 hours

Sources & evidence

ORD record
ord-49930358d06640d188bddafa0e81573d
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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