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

HRID 1986318Notes

Reaction equation

HRID 1986318 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18](Cl)[N:17]=4)[S:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(OC([N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][NH2:40])[C@@H:33]([CH3:41])[CH2:32]1)=O)(C)(C)C.[ClH:42]>Cl.Cl.ClC1C(C2SC3C=CC=C(C(N)=O)C=3C=2)=NC(NCCC2CCN(C)CC2)=NC=1>[ClH:22].[ClH:42].[ClH:22].[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:40][CH2:39][CH2:38][CH2:37][N:34]5[CH2:35][CH2:36][NH:31][CH2:32][C@@H:33]5[CH3:41])[N:17]=4)[S:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68857410(S)-4-(3-aminopropyl)-3-methylpiperazine-1-carboxylic acid tert-butyl esterHCID 866253512-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Product 1

HCID 68857432(S)-2-{5-Chloro-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide tri-hydrochloride

Reagents, catalysts & solvents 1

HCID 688560452-{5-Chloro-2-[2-(1-methylpiperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid amide di-hydrochlorideSolvent

Procedure

Using the method of (R)-2-{5-chloro-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide, free base of the title compound is synthesized from 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide and (S)-4-(3-aminopropyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester. After treating the free base with 12 N HCl (10 equivalents) as described in 2-{5-chloro-2-[2-(1-methylpiperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid amide di-hydrochloride, the title compound is isolated as a yellow solid. ES+(m/z) 485 (35Cl) and 487 (37Cl) [M(free base)+H].

Sources & evidence

ORD record
ord-4f907be2c6ef4942a4cd7cb8f4c749ad
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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