Ethyl Acetate → Methyl 2-(4-azepan-1-yl-3-cyanophenyl)isonicotinate

HRID 562915

Reaktionsgleichung

Reaktionsgleichung von HRID 562915
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1F)#[N:2].C(O[CH2:24][CH3:25])(=O)C>CS(C)=O>[N:2]1([C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=3)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=2[C:1]#[N:2])[CH2:25][CH2:24][CH2:7][CH2:8][CH2:3][CH2:1]1

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 66995083Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate

Produkt 1

HCID 66995069Methyl 2-(4-azepan-1-yl-3-cyanophenyl)isonicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In 7 ml of DMSO was dissolved 2.22 g of methyl 2-(3-cyano-4-fluorophenyl)isonicotinate, and 2.44 ml of hexamethyleneimine was added thereto, followed by heating at 50° C. for 5 hours. After cooling, the reaction solution was diluted with ethyl acetate and was washed with 1M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and brine, successively. The organic layer was dried and then concentrated under reduced pressure and the resulting residue was dissolved in a mixed solvent of ethyl acetate and diisopropyl ether. Activated carbon was added thereto, followed by stirring for 1 hour. Then, the activated carbon was removed by filtration and washed with ethyl acetate. The resulting filtrate and washing liquid were combined and concentrated to obtain 2.58 g of methyl 2-(4-azepan-1-yl-3-cyanophenyl)isonicotinate. (2) Then, 2.49 g of the compound was dissolved in a mixed solvent of 15 ml of methanol and 30 ml of THF, and 11 ml of a 1M aqueous sodium hydroxide solution was added thereto, followed by heating at 80° C. for 1 hour.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling
  3. washwas washed with 1M hydrochloric acid
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionthe resulting residue was dissolved in a mixed solvent of ethyl acetate and diisopropyl ether
  7. additionActivated carbon was added
  8. customThen, the activated carbon was removed by filtration
  9. washwashed with ethyl acetate
  10. washThe resulting filtrate and washing liquid
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-639eace32c3a47839a011c2662d7fe62
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067446B2

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