Potassium Acetate → HCID 22397176, compound

HRID 1070644Notes

Reaction equation

HRID 1070644 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10](Cl)[N:11]=[C:12]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:13]=2)[N:8]([CH3:25])[CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[K+]>C(O)(C)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][N:11]=[C:12]([CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH:13]=2)[N:8]([CH3:25])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 22397142HCID 22397142, compound

Product 1

HCID 22397176HCID 22397176, compoundYield 711.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl-8-chloro-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-[1,7]naphthyridine-3-carboxylate (Preparation 45, 0.090 g), potassium acetate (0.015 g) and 10% Pd/C (20 mg) in isopropyl alcohol is hydrogenated (balloon) for 18 hours. The mixture is filtered through celite and the filter cake washed with MeOH. The solvent is evaporated and the crude solid chromatographed with CH2Cl2\CH3OH\TEA (90\9\1) to obtain 0.58 g (70%) of the title compound as an off-white solid. Physical characteristics: MS (ESI+) m/z 332 (M+H).

Workup

  1. customfor 18 hours
  2. filtrationThe mixture is filtered through celite
  3. washthe filter cake washed with MeOH
  4. customThe solvent is evaporated
  5. customthe crude solid chromatographed with CH2Cl2\CH3OH\TEA (90\9\1)

Sources & evidence

ORD record
ord-0bb9612b346c4e9890b602e1185d6e83
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

Loading…