Dimethylformamide → HCID 22175803, compound

HRID 1797641Notes

Reaction equation

HRID 1797641 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]([Cl: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:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=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 22175872HCID 22175872, compound

Product 1

HCID 22175803HCID 22175803, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-[[(tert-butoxycarbonyl)amino]methyl]-4-(4-chlorophenyl)-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinecarboxamide (Example 186 (4)) (0.48 g, 1 mmol) and cyanuric chloride (0.55 g, 3 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[4-(4-chlorophenyl)-6-cyano-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.37 g, 80.4%) 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. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-55a4a6cac90b4900ad76d1ebaa41d164
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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