HCID 58455245, compound → HCID 58455284, compound

HRID 41820Notes

Reaction equation

HRID 41820 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([O:19][CH2:20][C@H:21]([CH3:22])[N:8]3[CH:7]=[C:6]([C:23]([O:25][CH:26]3[CH2:31][O:30]C(C4C=CC=CC=4)[O:28][CH2:27]3)=[O:24])[C:5]2=[O:38])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1>ClCCl.CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([O:19][CH2:20][C@H:21]([CH3:22])[N:8]3[CH:7]=[C:6]([C:23]([O:25][CH:26]([CH2:31][OH:30])[CH2:27][OH:28])=[O:24])[C:5]2=[O:38])[C:11]=1[N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 58455245HCID 58455245, compound

Product 1

HCID 58455284HCID 58455284, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

(S)-2-phenyl-1,3-dioxan-5-yl 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate (0.50 g, 9.55 mmol), was dissolved in a mixture of dichloromethane/methanol (2:1.5, 87.5 ml) under argon. Palladium catalyst (10 wt % Pd/C) (180 mg) was added, the flask was evacuated and allowed to stir 1 atm of hydrogen gas at room temperature for 16 hours. The crude reaction mixture was passed through a glass microfiber on a sintered funnel. The volatiles were removed under reduced pressure yielding 370 mg (88%) of a yellow gum.

Workup

  1. customthe flask was evacuated
  2. customThe crude reaction mixture
  3. customwas passed through a glass microfiber on a sintered funnel
  4. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-87686e373adb4397abcd1d54e8e1cafc
Source dataset
uspto-grants-2013_09
Patent number
US08535655B2

Reaction notes

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