Dimethylformamide dimethyl acetal → HCID 68697156, compound

HRID 2236960Notes

Reaction equation

HRID 2236960 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[NH:7][C:6](=[O:14])[CH2:5]2.[CH3:15]OC(N(C)C)OC.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1>CN(C=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])([CH3:13])[NH:7][C:6](=[O:14])[C:5]2=[CH:15][NH:36][C:33]1[CH:34]=[CH:35][C:30]([N:27]2[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]2)=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 59299845HCID 59299845, compound

Product 1

HCID 68697156HCID 68697156, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

6-Bromo-1,1-dimethyl-1,4-dihydro-2H-isoquinolin-3-one (210 mg, 0.83 mmol) and dimethoxymethyl-dimethyl-amine (250 mg, 2.1 mmol) in DMF (4 mL) is heated at 100° C. for 1 hour. After which the DMF is evaporated and toluene (6 mL) is added. This solution is then mixed with a solution of 4-(4-Methyl-piperazin-1-yl)-phenylamine (450 mg, 2.4 mmol) in toluene (4 mL) and the mixture is heated at reflux for 6 hours. The mixture is then allowed to cool to room temperature, upon cooling, precipitates formed. The precipitate is collected and further purified through chromatography to provide the title compound (120 mg, 31%). MS (ESI): 455.1, 457.1 (M+1)−1.

Workup

  1. customAfter which the DMF is evaporated
  2. additiontoluene (6 mL) is added
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 6 hours
  5. temperatureupon cooling
  6. customprecipitates
  7. customformed
  8. customThe precipitate is collected
  9. customfurther purified through chromatography

Sources & evidence

ORD record
ord-501a11c1294c4d39a9f7707bb32393bc
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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