Dimethylformamide → HCID 22175602, compound

HRID 1797626Notes

Reaction equation

HRID 1797626 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11](CC(C)C)[C:12](=[O:30])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([C:27]([NH2:29])=O)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.CN(C)C=O>O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[NH:11][C:12](=[O:30])[C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)=[CH:17][C:16]([C:27]#[N:29])=[CH:15][CH:14]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 22175203HCID 22175203, compound

Product 1

HCID 22175602HCID 22175602, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-4-(4-methylphenyl)-1-oxo-1,2-dihydro-6-isoquinolinecarboxamide (Example 3 (4)) (0.37 g, 0.8 mmol) and cyanuric chloride (0.44 g, 2.4 mmol) in N,N-dimethylformamide (10 mmol) was stirred at 0° C. for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was, purified by silica gel column chromatography to give tert-butyl[6-cyano-4-(4-methylphenyl)-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.32 g, 91.4%) as crystals.

Workup

  1. customwas stirred at 0° C. for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b155717b4a914b69be63bee7da961ed8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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