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 920484Notes

Reaction equation

HRID 920484 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-c6842aa5ae8a4e83a157fd2d9b2b2928
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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