1,5-Bis(2-pyridyl)-1,3,5-pentanetrione → 4,4''-di-pyrrolidin-1-yl-1'H-[2,2';6',2'']terpyridin-4'-one

HRID 640672Notes

Reaction equation

HRID 640672 reaction equation
[N:1]1C=CC=CC=1C(=O)CC(=O)CC(C1C=CC=CN=1)=O.[N:21]1([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([C:32](=O)[CH2:33][C:34](=[O:49])[CH2:35][C:36]([C:38]3[CH:43]=[C:42]([N:44]4[CH2:48][CH2:47][CH2:46][CH2:45]4)[CH:41]=[CH:40][N:39]=3)=O)[CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1>CO>[N:21]1([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([C:32]3[NH:1][C:36]([C:38]4[CH:43]=[C:42]([N:44]5[CH2:48][CH2:47][CH2:46][CH2:45]5)[CH:41]=[CH:40][N:39]=4)=[CH:35][C:34](=[O:49])[CH:33]=3)[CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 113691811,5-Bis(2-pyridyl)-1,3,5-pentanetrioneHCID 179719271,5-Bis(4-pyrrolidin-1-yl-pyridin-2-yl)-pentane-1,3,5-trione

Product 1

HCID 587814384,4''-di-pyrrolidin-1-yl-1'H-[2,2';6',2'']terpyridin-4'-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound is prepared in a manner analogous to that described in Example 1, Step 2 for 1,5-di-pyridin-2-yl-pentane-1,3,5-trione, but instead the pyrrolidine-substituted triketone from Example 21 is used. Pure 4,4″-di-pyrrolidin-1-yl-1′H-[2,2′;6′,2″]terpyridin-4′-one can be obtained by recrystallisation from methanol in the form of an almost colourless solid. 1.81-2.05 (m, 8H); 3.17-3.33 (m, 8H); 6.32 (dd, 2H, J=5.7, 2.3 Hz); 6.84 (d, 2H, J=2.3 Hz); 6.90 (s, 2H); 8.19 (d, 2H, J=5.7 Hz). MS (EI pos., 70 eV), m/z=387 ([M+]), 359 (100); 358 (85); 330 (20); 28 (60).

Workup

  1. customThis compound is prepared in a manner analogous to

Sources & evidence

ORD record
ord-f4b1bf404b4d4c218d9523cfa7e5d4ae
Source dataset
uspto-grants-2010_04
Patent number
US07692004B2

Reaction notes

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