2-{5-Chloro-2-[3-(4-ethylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochloride → 2-{5-Chloro-2-[3-(4-ethylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide di-hydrochloride

HRID 1986326Notes

Reaction equation

HRID 1986326 reaction equation
Cl.Cl.[CH:3]1([NH:6][C:7]([C:9]2[C:17]3[CH:16]=[C:15]([C:18]4[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:25][CH2:26][CH2:27][CH2:28][C:29]5([CH2:35][CH3:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)[N:19]=4)[S:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[O:8])CC1.CNC(C1C2C=C(C3C([Cl:56])=CN=C(Cl)N=3)SC=2C=CC=1)=O.C(OC(N1CCC(CCCN)(CC)CC1)=O)(C)(C)C>>[ClH:24].[ClH:56].[CH3:3][NH:6][C:7]([C:9]1[C:17]2[CH:16]=[C:15]([C:18]3[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:25][CH2:26][CH2:27][CH2:28][C:29]4([CH2:35][CH3:36])[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]4)[N:19]=3)[S:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 3

HCID 688557592-{5-Chloro-2-[3-(4-ethylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochlorideHCID 688567424-(3-Aminopropyl)-4-ethylpiperidine-1-carboxylic acid tert-butyl esterHCID 866253822-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methylamide

Product 1

HCID 688578252-{5-Chloro-2-[3-(4-ethylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide di-hydrochloride

Procedure

Using the method of 2-{5-chloro-2-[3-(4-ethylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochloride, the title compound is synthesized from 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methylamide and 4-(3-aminopropyl)-4-ethylpiperidine-1-carboxylic acid tert-butyl ester and isolated as a solid. ES+(m/z) 472 (35Cl) and 474 (37Cl) [M(free base)+H].

Workup

  1. customisolated as a solid

Sources & evidence

ORD record
ord-8b02b086825240eea7c3bab201935b0f
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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