4-Chloro-2-methoxypyridine-3-carbaldehyde → 2-(4-Chloro-2-methoxypyridin-3-yl)-6-(2-(dimethylamino)ethyl)-4-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69357Notes

Reaction equation

HRID 69357 reaction equation
[NH2:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:12])[N:6]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:5]2=[O:18].[Cl:20][C:21]1[C:26]([CH:27]=O)=[C:25]([O:29][CH3:30])[N:24]=[CH:23][CH:22]=1>CO.C(O)(=O)C>[Cl:20][C:21]1[CH:22]=[CH:23][N:24]=[C:25]([O:29][CH3:30])[C:26]=1[C:27]1[NH:11][C:10]2=[CH:9][C:8]3[C:7](=[O:12])[N:6]([CH2:13][CH2:14][N:15]([CH3:16])[CH3:17])[C:5](=[O:18])[C:4]=3[C:3]([CH3:19])=[C:2]2[N:1]=1

Participants

5

Reactant 2

HCID 534079284-Chloro-2-methoxypyridine-3-carbaldehydeHCID 666871575,6-Diamino-2-(2-(dimethylamino)ethyl)-4-methylisoindoline-1,3-dione

Product 1

HCID 666871562-(4-Chloro-2-methoxypyridin-3-yl)-6-(2-(dimethylamino)ethyl)-4-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5,6-diamino-2-(2-(dimethylamino)ethyl)-4-methylisoindoline-1,3-dione (0.36 g, 1.37 mmol) and 4-chloro-2-methoxynicotinaldehyde (0.26 g, 1.51 mmol) in a mixture of methanol (8 mL) and acetic acid (0.4 mL) was heated at 50° C. for 14 h. After the end of reaction was established by TLC, the reaction mixture was concentrated under vacuum to dryness, and the crude product was subjected to the next step without further purification. Mass (ESI, positive) m/z 414.1 [M+H]+.

Workup

  1. customAfter the end of reaction
  2. concentrationthe reaction mixture was concentrated under vacuum to dryness
  3. customthe crude product was subjected to the next step without further purification

Sources & evidence

ORD record
ord-a49710002dac4413934bf3f2c1103842
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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