(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-(3-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid methylamide

HRID 1986323Notes

Reaction equation

HRID 1986323 reaction equation
CNC(C1C2C=C(C3C(Cl)=CN=C(NCCCN4CCNC[C@H]4C)N=3)SC=2C=CC=1)=O.[CH3:32][NH:33][C:34]([C:36]1[C:44]2[CH:43]=[C:42]([C:45]3[C:50]([CH3:51])=[CH:49][N:48]=[C:47](Cl)[N:46]=3)[S:41][C:40]=2[CH:39]=[CH:38][CH:37]=1)=[O:35].C(OC([N:60]1[CH2:65][CH2:64][N:63]([CH2:66][CH2:67][CH2:68][NH2:69])[CH2:62][C@@H:61]1[CH3:70])=O)(C)(C)C>>[CH3:32][NH:33][C:34]([C:36]1[C:44]2[CH:43]=[C:42]([C:45]3[C:50]([CH3:51])=[CH:49][N:48]=[C:47]([NH:69][CH2:68][CH2:67][CH2:66][N:63]4[CH2:64][CH2:65][NH:60][C@@H:61]([CH3:70])[CH2:62]4)[N:46]=3)[S:41][C:40]=2[CH:39]=[CH:38][CH:37]=1)=[O:35]

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 68857024(S)-4-(3-aminopropyl)-2-methylpiperazine-1-carboxylic acid tert-butyl esterHCID 866253842-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid methylamide

Product 1

HCID 68856782(S)-2-{5-Methyl-2-[3-(3-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)-2-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-2e7ccfdd070a4515a9bbb73732d36b1a
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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