Hydrochloric Acid → HCID 22470068, compound

HRID 394978Notes

Reaction equation

HRID 394978 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:29]([O:31]CC)=[O:30])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH2:17][CH2:16]1)=[CH:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2.Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:29]([OH:31])=[O:30])[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][S:23][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH2:19][CH2:20]1)=[CH:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22468467HCID 22468467, compound

Product 1

HCID 22470068HCID 22470068, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.4 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-carboxylate in 5 cm3 of aqueous 5N hydrochloric acid and 3 cm3 of dioxane was maintained at a temperature in t h e region of 100° C. with stirring and under an inert atmosphere for 20 hours. After cooling to about 20° C., the reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The mixture was filtered and then chromatographed, under atmospheric pressure, on a column of silica gel (particle size 40-63μ; diameter 1.5 cm; mass 55 g), eluting with a mixture of chloroform/methanol/aqueous ammonia (12/3/0.5 by volume) and collecting 15-cm3 fractions. Fractions 5 to 12 were combined and then concentrated to dryness under the above conditions. 0.26 g of 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylic acid was obtained in the form of a white crystalline solid melting at 180° C.

Workup

  1. temperatureAfter cooling to about 20° C.
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. filtrationThe mixture was filtered
  4. customchromatographed, under atmospheric pressure, on a column of silica gel (particle size 40-63μ; diameter 1.5 cm; mass 55 g)
  5. washeluting with a mixture of chloroform/methanol/aqueous ammonia (12/3/0.5 by volume)
  6. customcollecting 15-cm3 fractions
  7. concentrationconcentrated to dryness under the above conditions

Sources & evidence

ORD record
ord-3d0c210608af45e081cce8090b51067c
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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