N-(2-amino-4-chloro-5-(trifluoromethyl)phenyl)-3-(3-oxocyclobutyl)propanamide → HCID 178515984, Verbindung

HRID 511605

Reaktionsgleichung

Reaktionsgleichung von HRID 511605
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:13][C:14](=O)[CH2:15][CH2:16][CH:17]1[CH2:20][C:19](=[O:21])[CH2:18]1>C(O)(=O)C>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]2[N:13]=[C:14]([CH2:15][CH2:16][CH:17]3[CH2:20][C:19](=[O:21])[CH2:18]3)[NH:1][C:2]=2[CH:7]=1

Komponenten

3

Edukt 1

HCID 67773908N-(2-amino-4-chloro-5-(trifluoromethyl)phenyl)-3-(3-oxocyclobutyl)propanamide

Produkt 1

HCID 178515984HCID 178515984, VerbindungAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

N-(2-amino-4-chloro-5-(trifluoromethyl)phenyl)-3-(3-oxocyclobutyl)propanamide (72 mg, mmol) was taken up in acetic acid (3.2 mL) and the solution was heated at 65° C. for 26 h, upon which HPLC indicated the starting material was consumed and a new product had formed. The reaction mixture was cooled and the solvent was removed under high vac. The light brown residue was taken up in 20 mL ethyl acetate and the organic phase was washed with 10 mL portions of sat NaHCO3 and H2O. The organic phase was dried over Na2SO4, filtered and concentrated to yield a light brown glass. The crude material was purified by prep TLC (20 cm×20 cm×1.0 mm prep TLC plate, 3% MeOH/EA) to yield the title compound (45 mg, 66%) as a tan glass: MS (ESI+) for C14H12ClF3N2O m/z 317.2 (M+H)+; MS (ESI−) for C14H12ClF3N2O m/z 315.2 (M−H)−; HPLC purity 84.1% (ret. time, 2.98 min).

Aufarbeitung

  1. customwas consumed
  2. customa new product had formed
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed under high vac
  5. washthe organic phase was washed with 10 mL portions of sat NaHCO3 and H2O
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a light brown glass
  10. customThe crude material was purified by prep TLC (20 cm×20 cm×1.0 mm prep TLC plate, 3% MeOH/EA)

Quellen und Nachweise

ORD-Eintrag
ord-ef64d264029148b2b8c93d8b2b8d5684
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096634B2

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