Hydrochloric Acid → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

HRID 41170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41170
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[CH:17]=[C:18]([C:33]([O:35]C)=[O:34])[CH:19]=[C:20]3[C:25]=2[O:24][C:23]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:22][C:21]3=[O:32])[CH:7]=[C:8]([F:10])[CH:9]=1.Cl>CO>[F:3][C:4]1[CH:5]=[C:6]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[CH:17]=[C:18]([C:33]([OH:35])=[O:34])[CH:19]=[C:20]3[C:25]=2[O:24][C:23]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)=[CH:22][C:21]3=[O:32])[CH:7]=[C:8]([F:10])[CH:9]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86672406methyl 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Produkt 1

HCID 866724028-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acidAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

An aqueous NaOH 2N (0.622 mL, 1.24 mmol) solution was added to methyl 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (195 mg, 0.41 mmol) in MeOH (2 mL) and the reaction mixture stirred at 40° C. for 6 h. The mixture was cooled to 0° C. and an aqueous HCl 2N (0.684 mL, 1.37 mmol) solution was added dropwise to the reaction mixture until pH ˜5. The solution was partially concentrated and a precipitate appeared. Water was added to the slurry and extracted with DCM. The organic phase was washed with water, dried over MgSO4, filtered and concentrated. The formed precipitate was triturated with ether, filtered, washed with ether, dried under vacuum at 50° C. to afford 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (67 mg, 35%) as a pale beige solid. Mass Spectrum: m/z [M+H]+=457.

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. concentrationThe solution was partially concentrated
  3. additionWater was added to the slurry
  4. extractionextracted with DCM
  5. washThe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe formed precipitate was triturated with ether
  10. filtrationfiltered
  11. washwashed with ether
  12. customdried under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-8b838650d64b461fa655d81b1cb228f7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530470B2

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