Hydroxyamine hydrochloride → Methyl (3RS,4RS)-4-[3-hydroxyimino-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl)-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate

HRID 394710Notes

Reaction equation

HRID 394710 reaction equation
Cl.[NH2:2][OH:3].O=[C:5]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][C:28]=1[F:39])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH:9]1[CH2:22][C:23]([O:25][CH3:26])=[O:24]>N1C=CC=CC=1>[OH:3][N:2]=[C:5]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][C:28]=1[F:39])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH:9]1[CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 91496628methyl (3RS,RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl)-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate

Product 1

HCID 137178928Methyl (3RS,4RS)-4-[3-hydroxyimino-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl)-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

0.363 g of hydroxylamine hydrochloride was added in several portions to a mixture of 0.99 g of methyl (3RS,RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl)-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate in 10-cm3 of pyridine, with stirring and under an inert atmosphere, and the resulting mixture was heated in the region of 60° C. for 16 hours. After cooling in the region of 20° C., the reaction mixture was concentrated to dryness under reduced pressure (8 kPa) at a temperature in the region of 55° C. The evaporation residue was taken up in 75-cm3 of ethyl acetate and 40-cm3 of distilled water. The organic phase was washed three times with 40-cm3 of distilled water and 40-cm3 of a saturated sodium chloride solution, dried over magnesium sulfate for 30 minutes, filtered and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.98 g of methyl (3RS,4RS)-4-[3-hydroxyimino-3-(fluoro-6-methoxyquinolin-4-yl)propyl)-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate wereobtained in the form of a yellow gum.

Workup

  1. temperatureAfter cooling in the region of 20° C.
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (8 kPa) at a temperature in the region of 55° C
  3. washThe organic phase was washed three times with 40-cm3 of distilled water and 40-cm3 of a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate for 30 minutes
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-f1a86780c11043da88b8da987822ca83
Source dataset
uspto-grants-2003_08
Patent number
US06602884B2

Reaction notes

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