(R)-2-{5-Chloro-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide → (S)-2-{5-Methyl-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

HRID 1986320Notes

Reaction equation

HRID 1986320 reaction equation
CNC(C1C2C=C(C3C(Cl)=CN=C([NH:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][C@H:26]4[CH3:31])N=3)SC=2C=CC=1)=O.[CH:32]1([NH:35][C:36]([C:38]2[C:46]3[CH:45]=[C:44]([C:47]4[C:52]([CH3:53])=[CH:51][N:50]=[C:49](Cl)[N:48]=4)[S:43][C:42]=3[CH:41]=[CH:40][CH:39]=2)=[O:37])[CH2:34][CH2:33]1.C(OC(N1CCN(CCCN)[C@@H](C)C1)=O)(C)(C)C>>[CH:32]1([NH:35][C:36]([C:38]2[C:46]3[CH:45]=[C:44]([C:47]4[C:52]([CH3:53])=[CH:51][N:50]=[C:49]([NH:21][CH2:22][CH2:23][CH2:24][N:25]5[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]5[CH3:31])[N:48]=4)[S:43][C:42]=3[CH:41]=[CH:40][CH:39]=2)=[O:37])[CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 68856124(R)-2-{5-Chloro-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamideHCID 68857410(S)-4-(3-aminopropyl)-3-methylpiperazine-1-carboxylic acid tert-butyl esterHCID 866253772-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Product 1

HCID 68908164(S)-2-{5-Methyl-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Procedure

Using the method of (R)-2-{5-chloro-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide, the title compound is synthesized from 2-(2-chloro-5-methyl-pyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide and (S)-4-(3-aminopropyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester and isolated as a yellow solid. ES+(m/z) 465 [M+H].

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-c0d9c2bf94024bc285ab3a6512c4c167
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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