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

HRID 1986278Notes

Reaction equation

HRID 1986278 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21](F)=[CH:20][N:19]=[C:18]([NH:23]CCCC5CCNCC5)[N:17]=4)[S:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[O:6])CC1.[ClH:33].Cl.C1(NC(C2C3C=C(C4C(F)=CN=C(NC[CH2:59][CH2:60][CH:61]5[CH2:66][CH2:65][N:64]([CH3:67])[CH2:63][CH2:62]5)N=4)SC=3C=CC=2)=O)CC1.CNC(C1C2C=C(C3C([Cl:87])=CN=C(Cl)N=3)SC=2C=CC=1)=O>>[ClH:87].[ClH:33].[CH3:1][NH:4][C:5]([C:7]1[C:15]2[CH:14]=[C:13]([C:16]3[C:21]([Cl:87])=[CH:20][N:19]=[C:18]([NH:23][CH2:59][CH2:60][CH:61]4[CH2:66][CH2:65][N:64]([CH3:67])[CH2:63][CH2:62]4)[N:17]=3)[S:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:6]

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 688570822-{5-Chloro-2-[2-(1-methyl-piperidin-4-yl)-ethylamino]-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) 444 (35Cl) and 446 (37Cl) [M(free base)+H].

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-c77a56d87b6749f6bacf4eecc9db3134
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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