[4-(6'-Methylamino-[2,2';4',3'']terpyridin-5''-yl)-phenyl]-(4-methyl-piperazin-1-yl)-methanone → {5''-[4-(4-Isopropyl-piperazin-1-ylmethyl)-phenyl]-[2,2';4',3'']terpyridin-6'-yl}-dimethyl-amine

HRID 1798527Notes

Reaction equation

HRID 1798527 reaction equation
CNC1N=C(C2C=CC=CN=2)C=C(C2C=NC=C(C3C=CC(C(N4CCN(C)CC4)=O)=CC=3)C=2)C=1.Br[C:37]1[CH:38]=[C:39]([C:43]2[CH:48]=[C:47]([N:49]([CH3:51])[CH3:50])[N:46]=[C:45]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=3)[CH:44]=2)[CH:40]=[N:41][CH:42]=1.[CH:58]([N:61]1[CH2:66][CH2:65][N:64]([CH2:67][C:68]2[CH:73]=[CH:72][C:71](B(O)O)=[CH:70][CH:69]=2)[CH2:63][CH2:62]1)([CH3:60])[CH3:59]>>[CH:58]([N:61]1[CH2:62][CH2:63][N:64]([CH2:67][C:68]2[CH:73]=[CH:72][C:71]([C:37]3[CH:38]=[C:39]([C:43]4[CH:48]=[C:47]([N:49]([CH3:51])[CH3:50])[N:46]=[C:45]([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=5)[CH:44]=4)[CH:40]=[N:41][CH:42]=3)=[CH:70][CH:69]=2)[CH2:65][CH2:66]1)([CH3:60])[CH3:59]

Participants

4

Reactant 3

HCID 44136079[4-(6'-Methylamino-[2,2';4',3'']terpyridin-5''-yl)-phenyl]-(4-methyl-piperazin-1-yl)-methanoneHCID 615342304-((4-Isopropyl-piperazin-1-yl)methyl)-phenyl boronic acid2×HCID 68735749(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-dimethyl-amine

Product 1

HCID 68758499{5''-[4-(4-Isopropyl-piperazin-1-ylmethyl)-phenyl]-[2,2';4',3'']terpyridin-6'-yl}-dimethyl-amine

Procedure

This compound is prepared analogously to [4-(6′-Methylamino-[2,2′;4′,3″]terpyridin-5″-yl)-phenyl]-(4-methyl-piperazin-1-yl)-methanone (Example 2.1) by replacing (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-methyl-amine (Example 2.1 step1) with (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-dimethyl-amine and by replacing (4-Methyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone with 4-(4-Isopropyl-piperazin-1-ylmethyl)-phenyl boronic acid (Intermediate B3).

Sources & evidence

ORD record
ord-1754f9dde2bd45f99816851b754bf09a
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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