2-[5-Fluoro-2-(3-piperidin-4-ylpropylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid cyclopropylamide → 2-{5-Chloro-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide di-hydrochloride

HRID 1986279Notes

Reaction equation

HRID 1986279 reaction equation
C1(NC(C2C3C=C(C4C(F)=CN=C(NCCCC5CCNCC5)N=4)SC=3C=CC=2)=O)CC1.[ClH:33].Cl.[CH:35]1([NH:38][C:39]([C:41]2[C:49]3[CH:48]=[C:47]([C:50]4[C:55](F)=[CH:54][N:53]=[C:52]([NH:57][CH2:58][CH2:59][CH2:60][CH:61]5[CH2:66][CH2:65][N:64]([CH3:67])[CH2:63][CH2:62]5)[N:51]=4)[S:46][C:45]=3[CH:44]=[CH:43][CH:42]=2)=[O:40])CC1.CNC(C1C2C=C(C3C([Cl:87])=CN=C(Cl)N=3)SC=2C=CC=1)=O>>[ClH:87].[ClH:33].[CH3:35][NH:38][C:39]([C:41]1[C:49]2[CH:48]=[C:47]([C:50]3[C:55]([Cl:87])=[CH:54][N:53]=[C:52]([NH:57][CH2:58][CH2:59][CH2:60][CH:61]4[CH2:66][CH2:65][N:64]([CH3:67])[CH2:63][CH2:62]4)[N:51]=3)[S:46][C:45]=2[CH:44]=[CH:43][CH:42]=1)=[O:40]

Participants

4

Reactant 3

HCID 688563522-[5-Fluoro-2-(3-piperidin-4-ylpropylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid cyclopropylamideHCID 688573542-{5-Fluoro-2-[3-(1-methylpiperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide di-hydrochlorideHCID 866253822-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methylamide

Product 1

HCID 689095692-{5-Chloro-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide di-hydrochloride

Procedure

Using the methods of 2-[5-fluoro-2-(3-piperidin-4-ylpropylamino)-pyrimidin-4-yl]-benzo[b]thiophene-4-carboxylic acid cyclopropylamide and 2-{5-fluoro-2-[3-(1-methylpiperidin-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 isolated as a yellow solid. ES+(m/z) 458 (35Cl) and 460 (37Cl) [M(free base)+H].

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-43dba17042944bbabdc56da15589fef1
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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