(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 methylamide

HRID 1986319Notes

Reaction equation

HRID 1986319 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([C:14]3[C:19](Cl)=[CH:18][N:17]=[C:16]([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:15]=3)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:32]NC(C1C2C=C(C3C(C)=CN=C(Cl)N=3)SC=2C=CC=1)=O.C(OC(N1CCN(CCCN)[C@@H](C)C1)=O)(C)(C)C>>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([C:14]3[C:19]([CH3:32])=[CH:18][N:17]=[C:16]([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:15]=3)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

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 866253842-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methylamide

Product 1

HCID 68909828(S)-2-{5-Methyl-2-[3-(2-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide

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-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methylamide and (S)-4-(3-aminopropyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester and isolated as a yellow solid. ES+(m/z) 439 [M+H].

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-b0ac94eefa4b44b78d4fff53b87f7711
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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