[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]-6'-pyrrolidin-1-yl-[2,2';4',3'']terpyridine

HRID 1798528Notes

Reaction equation

HRID 1798528 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]3[CH2:53][CH2:52][CH2:51][CH2:50]3)[N:46]=[C:45]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=3)[CH:44]=2)[CH:40]=[N:41][CH:42]=1.[CH:60]([N:63]1[CH2:68][CH2:67][N:66]([CH2:69][C:70]2[CH:75]=[CH:74][C:73](B(O)O)=[CH:72][CH:71]=2)[CH2:65][CH2:64]1)([CH3:62])[CH3:61]>>[CH:60]([N:63]1[CH2:64][CH2:65][N:66]([CH2:69][C:70]2[CH:75]=[CH:74][C:73]([C:37]3[CH:38]=[C:39]([C:43]4[CH:48]=[C:47]([N:49]5[CH2:53][CH2:52][CH2:51][CH2:50]5)[N:46]=[C:45]([C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=5)[CH:44]=4)[CH:40]=[N:41][CH:42]=3)=[CH:72][CH:71]=2)[CH2:67][CH2:68]1)([CH3:62])[CH3:61]

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 687586905''-Bromo-6'-pyrrolidin-1-yl-[2,2';4',3'']terpyridine

Product 1

HCID 687586805''-[4-(4-Isopropyl-piperazin-1-ylmethyl)-phenyl]-6'-pyrrolidin-1-yl-[2,2';4',3'']terpyridine

Procedure

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-6′-pyrrolidin-1-yl-[2,2′;4′,3″]terpyridine 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-cb3cc37f092b41ff922f3de6eb0736b0
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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