HCID 13005739, compound → HCID 86642360, compound

HRID 2383239Notes

Reaction equation

HRID 2383239 reaction equation
[NH2:1][C:2]1[N:3]([CH2:18][CH3:19])[C:4]2[C:9]([C:10](=[O:16])[C:11]=1[C:12]([NH:14][CH3:15])=[O:13])=[CH:8][CH:7]=[C:6](Cl)[N:5]=2.[CH3:20][C:21]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:24])[C:22]#[CH:23]>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]([CH2:18][CH3:19])[C:4]2[N:5]=[C:6]([C:23]#[C:22][C:21]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:24])[CH3:20])[CH:7]=[CH:8][C:9]=2[C:10](=[O:16])[C:11]=1[C:12](=[O:13])[NH:14][CH3:15]

Participants

8

Reactant 2

HCID 13005739HCID 13005739, compoundHCID 866423362-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 86642360HCID 86642360, compoundYield 82.4%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1.15 g (4.10 mmol) of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide and 1.39 g (8.19 mmol) of ethyl [(1,1-dimethylprop-2-yn-1-yl)oxy]acetate are placed in a mixture of 10 ml of dimethylformamide and 10 ml of triethylamine. Argon is sparged into the reaction mixture for 15 minutes and then 0.031 g (0.16 mmol) of CuI and 0.144 g (0.20 mmol) of bis(triphenylphosphine)palladium(II) dichloride are successively added. The reaction mixture is heated at 90° C. for 15 hours. After returning to ambient temperature, the reaction mixture is poured onto a water/ice mixture. After separating them by settling, the black gum obtained is dissolved in ethyl acetate and then washed with water. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. 1.4 g of a brown oil are obtained, which oil is purified by chromatography on silica (elution with a cyclohexane/ethyl acetate 30:70 to 20:80 gradient) to give 0.72 g of the expected product in the form of a yellow solid.

Workup

  1. customArgon is sparged into the reaction mixture for 15 minutes
  2. customAfter returning to ambient temperature
  3. customAfter separating them
  4. customthe black gum obtained
  5. washwashed with water
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-01ec12bdba234afe9280f3d1b79b284f
Source dataset
uspto-grants-2012_09
Patent number
US08263614B2

Reaction notes

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