Acetonitrile → HCID 22106040, compound

HRID 1456394Notes

Reaction equation

HRID 1456394 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)=[C:7]([NH:22][C:23]([NH:25][C:26]2[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=2[CH:35]([CH3:37])[CH3:36])=[O:24])[C:6]1=[O:38])[CH2:2][CH2:3][CH3:4].C1(P([C:52]2[CH:57]=[CH:56]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:58]([N:60](CC)[CH2:61][CH3:62])[CH3:59].C(#N)C>[Cu]I.[C].[Pd].CN(C=O)C>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:52]#[C:57][CH2:56][N:60]([CH2:61][CH3:62])[CH2:58][CH3:59])[CH:16]=2)=[C:7]([NH:22][C:23]([NH:25][C:26]2[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=2[CH:35]([CH3:37])[CH3:36])=[O:24])[C:6]1=[O:38])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 22106357HCID 22106357, compound

Product 1

HCID 22106040HCID 22106040, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[1-butyl-4-(3-bromophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (4.6 g, 8 mmol), 3-diethylamino-3-propyne (2.67 g, 24 mmol), copper (I) iodide (122 mg, 0.64 mmol), triphenylphosphine (335 mg, 1.28 mmol), 10% palladium-carbon (336 mg), triethylamine (30 ml), acetonitrile (30 ml), and DMF (30 ml) was heated under reflux for six hours. After allowed to stand for cooling, the mixture was filtered through a cerite pad. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (500 ml). The mixture was washed with water, washed with a 0.5N aqueous hydrochloric acid solution, washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0-4% methanol in chloroform) to give the title compound (3.05g, 5.0 mmol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for six hours
  3. temperaturefor cooling
  4. filtrationthe mixture was filtered through a cerite pad
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate (500 ml)
  7. washThe mixture was washed with water
  8. washwashed with a 0.5N aqueous hydrochloric acid solution
  9. washwashed with water
  10. washwashed with a saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationThe resultant was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (0-4% methanol in chloroform)

Sources & evidence

ORD record
ord-4ba973c9b875429ab906d05d3b7fcd25
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

Loading…