Acetic Acid → 2-(4-Iodo-2-methoxy-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione

HRID 561908Notes

Reaction equation

HRID 561908 reaction equation
[NH2:1][C:2]1[C:3]([CH3:21])=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:12])[N:6]([CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[C:5]2=[O:20].CC(O)=O.[I:26][C:27]1[C:32]([CH:33]=O)=[C:31]([O:35][CH3:36])[N:30]=[CH:29][CH:28]=1>CO>[I:26][C:27]1[CH:28]=[CH:29][N:30]=[C:31]([O:35][CH3:36])[C:32]=1[C:33]1[NH:11][C:10]2[C:2]([N:1]=1)=[C:3]([CH3:21])[C:4]1[C:5](=[O:20])[N:6]([CH:13]3[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)[C:7](=[O:12])[C:8]=1[CH:9]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 597617275,6-Diamino-4-methyl-2-(1-methyl-piperidin-4-yl)-isoindole-1,3-dione

Product 1

HCID 597620172-(4-Iodo-2-methoxy-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dioneYield 47.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5,6-Diamino-4-methyl-2-(1-methyl-piperidin-4-yl)-isoindole-1,3-dione (1.7 g, 5.90 mmol) in MeOH (50 mL) were added AcOH (3 mL) and 4-iodo-2-methoxynicotinaldehyde (1.55 g, 5.90 mmol) and the resulting mixture was heated at 60° C. for overnight. The reaction mixture was evaporated in vacuo and the residue was purified by flash chromatography (5-10% (6% NH3 in MeOH)/CHCl3) to afford 2-(4-Iodo-2-methoxy-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione (1.48 g, 47%) as a yellow solid.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was purified by flash chromatography (5-10% (6% NH3 in MeOH)/CHCl3)

Sources & evidence

ORD record
ord-c13755a180da485781ab2f04436d6135
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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