Propargyl alcohol → HCID 22105947, compound

HRID 1456392Notes

Reaction equation

HRID 1456392 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].[CH2:39]([OH:42])[C:40]#[CH:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)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:41]#[C:40][CH2:39][OH:42])[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

10

Reactant 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 22106357HCID 22106357, compound

Product 1

HCID 22105947HCID 22105947, compoundYield 3%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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 (575 mg, 1 mmol), propargyl alcohol (168 mg, 3 mmol), copper (I) iodide (38 mg, 0.2 mmol), triphenylphosphine (52 mg, 0.2 mmol), bis(triphenylphosphine)palladium (II) chloride (14 mg, 0.02 mmol), triethylamine (5 ml) and acetonitrile (5 ml) was heated under reflux for five hours. After allowed to stand for cooling, the mixture was diluted with a mixture of tetrahydrofuran and ethyl acetate, and the mixture was filtered through a cerite pad. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The resultant was washed with 0.1N aqueous hydrochloric acid solution, washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3~5:5), and further purified by thin layer chromatography (hexane:ethyl acetate=5:5) to give the title compound (16 mg, 0.03 mmol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for five 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
  7. washThe resultant was washed with 0.1N aqueous hydrochloric acid solution
  8. washwashed with water
  9. washwashed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationThe resultant was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3~5:5)
  13. customfurther purified by thin layer chromatography (hexane:ethyl acetate=5:5)

Sources & evidence

ORD record
ord-6d57604e125149fc9c0547f271cfb75f
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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