Pyridine → HCID 57558196, compound

HRID 1162898Notes

Reaction equation

HRID 1162898 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.N1C=CC=CC=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[CH3:42][O:43][CH:44]([O:48][CH3:49])CNC.[CH3:50][N:51]([CH:53]=[O:54])[CH3:52]>C(Cl)Cl.O>[CH3:42][O:43][CH:44]([O:48][CH3:49])[CH2:50][N:51]([CH3:52])[C:53]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:20])[F:21])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:54]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 85032,2-DimethoxyethylmethylamineHCID 821294-Nitrophenyl chloroformateHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 57558196HCID 57558196, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (30.4 mg, 0.1 mmol) obtained in step C of Example 1-1 was dissolved in a mixed solvent (0.5 ml) of methylene chloride and DMF (1:1). Thereafter, pyridine (16.2 μl, 0.2 mmol) and 4-nitrophenyl chloroformate (24.2 mg, 0.12 mmol) were added thereto under cooling on ice. The obtained mixture was then stirred at a room temperature for 2 hours. Thereafter, 2,2-dimethoxy-N-methylethylamine (15.4 μl, 0.12 mmol) was added to the reaction solution, and the obtained mixture was then stirred at a room temperature overnight. Thereafter, water was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:1), so as to obtain 1-(2,2-dimethoxyethyl)-1-methyl-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]urea (17.5 mg; yield: 39%) in the form of a colorless amorphous substance.

Workup

  1. temperatureunder cooling on ice
  2. stirringthe obtained mixture was then stirred at a room temperature overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:1)

Sources & evidence

ORD record
ord-1ad25efa99c944008615bd6fd34b02d9
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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