2-{5-Chloro-2-[3-(1-cyclopropylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochloride → 2-{5-Bromo-2-[2-(1-cyclopropylpiperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide di-hydrochloride

HRID 1986281Notes

Reaction equation

HRID 1986281 reaction equation
[ClH:1].Cl.[CH:3]1(NC(C2C3C=C(C4C([Cl:24])=CN=C(NCCCC5CCN(C6CC6)CC5)N=4)SC=3C=CC=2)=O)[CH2:5][CH2:4]1.[CH3:38][NH:39][C:40]([C:42]1[C:50]2[CH:49]=[C:48]([C:51]3[C:56]([Br:57])=[CH:55][N:54]=[C:53]([NH:58][CH2:59][CH2:60][CH:61]4[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]4)[N:52]=3)[S:47][C:46]=2[CH:45]=[CH:44][CH:43]=1)=[O:41]>>[ClH:24].[ClH:1].[CH3:38][NH:39][C:40]([C:42]1[C:50]2[CH:49]=[C:48]([C:51]3[C:56]([Br:57])=[CH:55][N:54]=[C:53]([NH:58][CH2:59][CH2:60][CH:61]4[CH2:62][CH2:63][N:64]([CH:3]5[CH2:5][CH2:4]5)[CH2:65][CH2:66]4)[N:52]=3)[S:47][C:46]=2[CH:45]=[CH:44][CH:43]=1)=[O:41]

Participants

3

Reactant 2

HCID 688568892-{5-Chloro-2-[3-(1-cyclopropylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochlorideHCID 688578602-[5-Bromo-2-(2-piperidin-4-yl-ethylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid methylamide

Product 1

HCID 688573912-{5-Bromo-2-[2-(1-cyclopropylpiperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide di-hydrochloride

Procedure

Using the method of 2-{5-chloro-2-[3-(1-cyclopropylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochloride, the title compound is synthesized from 2-[5-bromo-2-(2-piperidin-4-yl-ethylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid methylamide and isolated as a yellow solid. ES+(m/z) 514 (79Br) and 516 (81Br) [M(free base)+H].

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-6d52efbf6960447988b41f947e14e6f7
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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