(R)-4-(2-aminoethyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester → (R)-2-{5-Methyl-2-[2-(2-methylpiperazin-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

HRID 1986315Notes

Reaction equation

HRID 1986315 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)=[CH:20][N:19]=[C:18]([NH:23][CH2:24][CH2:25][N:26]5[CH2:31][CH2:30][NH:29][CH2:28][C@H:27]5[CH3:32])[N:17]=4)[S:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[CH:33]1(NC(C2C3C=C(C4C(C)=CN=C(Cl)N=4)SC=3C=CC=2)=O)CC1.C(OC(N1CCN(CCN)[C@H](C)C1)=O)(C)(C)C>>[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([CH3:33])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][CH2:25][N:26]5[CH2:31][CH2:30][NH:29][CH2:28][C@H:27]5[CH3:32])[N:17]=4)[S:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 68856977(R)-4-(2-aminoethyl)-3-methylpiperazine-1-carboxylic acid tert-butyl esterHCID 68858225(R)-2-{5-Chloro-2-[2-(2-methylpiperazin-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamideHCID 866253772-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Product 1

HCID 68857496(R)-2-{5-Methyl-2-[2-(2-methylpiperazin-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Procedure

Using the method of (R)-2-{5-chloro-2-[2-(2-methylpiperazin-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide, the title compound is synthesized from 2-(2-chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide and (R)-4-(2-aminoethyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester and isolated as a yellow solid. ES+(m/z) 451 [M+H].

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-1d4f8555cf9b4e83bc40207793b9c9bb
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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