Phenyl chloroformate → HCID 9893095, compound

HRID 380167Notes

Reaction equation

HRID 380167 reaction equation
[NH2:1][C:2]1[C:3](=[O:24])[N:4]([CH2:20][CH2:21][CH2:22][CH3:23])[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[C:25](Cl)(=O)[O:26]C1C=CC=CC=1.[CH:35]([C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH:45]([CH3:47])[CH3:46])[C:39]=1[NH2:40])([CH3:37])[CH3:36]>O1CCCC1.CN(C)C1C=CN=CC=1.O.CN(C)C=O>[CH2:20]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][N:6]=2)[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:2]([NH:1][C:25]([NH:40][C:39]2[C:38]([CH:35]([CH3:37])[CH3:36])=[CH:44][CH:43]=[CH:42][C:41]=2[CH:45]([CH3:47])[CH3:46])=[O:26])[C:3]1=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 3

HCID 15891Phenyl chloroformateHCID 32484DiisopropylanilineHCID 11232543HCID 11232543, compound

Product 1

HCID 9893095HCID 9893095, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 3-amino-1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine (1.70 g, 5.26 mmol) in tetrahydrofuran (14 ml) was added phenyl chlorocarbonate (1.32 ml, 10.5 ml), and the mixture was stirred at 40-50° C. for 3 hours. The mixture was allowed to cool, and thereto was added water, and the mixture was extracted with water. The extract was washed with a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in dimethylformamide (10 ml), and thereto was added a solution of 2,6-diisopropylaniline (1.24 g, 6.31 mmol) and dimethylformamide (5 ml) and 4-dimethylaminopyridine (0.62 g, 5.26 mmol), and the mixture was stirred at room temperature for one hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed successively with a 5% aqueous sodium hydrogen carbonate solution and a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (1.75 g, 3.32 mmol) as colorless crystals.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with water
  3. washThe extract was washed with a 5% aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in dimethylformamide (10 ml)
  7. stirringthe mixture was stirred at room temperature for one hour
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed successively with a 5% aqueous sodium hydrogen carbonate solution
  10. dry with materiala 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ee69487bca304e8ca588693973688bc3
Source dataset
uspto-grants-2001_10
Patent number
US06300500B1

Reaction notes

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