1,2-Dichloroethane → 2,2-Dimethyl-N-[1-[6-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,2,4-oxadiazol-3-yl)quinolin-2-yl]pyrrolidin-3-yl}propanamide

HRID 6815

Reaktionsgleichung

Reaktionsgleichung von HRID 6815
[OH:1][NH:2][C:3](=[NH:26])[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:14]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15]1)[CH:8]=[CH:7]2.[F:27][C:28]([F:41])([F:40])[C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:39])C(O)=O)=[CH:31][CH:30]=1.[CH2:42](Cl)CCl>COCCOCCOC>[CH3:24][C:21]([CH3:22])([CH3:23])[C:20]([NH:19][CH:16]1[CH2:17][CH2:18][N:14]([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:3]4[N:26]=[C:42]([CH2:39][CH2:35][C:32]5[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:40])[F:41])=[CH:34][CH:33]=5)[O:1][N:2]=4)[CH:5]=3)[N:10]=2)[CH2:15]1)=[O:25]

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 102424842-(4-(Trifluoromethyl)phenyl)propanoic acidHCID 178419012HCID 178419012, Verbindung

Produkt 1

HCID 220189022,2-Dimethyl-N-[1-[6-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,2,4-oxadiazol-3-yl)quinolin-2-yl]pyrrolidin-3-yl}propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of the product of Step E, (66 mg) in anhydrous diglyme (2 mL) was added 4-trifluoromethylphenylpropionic acid (1.1 eq.) and EDC (2 eq.). The reaction mixture was heated to 50° C. overnight. After approximately 18 h, the mixture was heated at 110° C. for 2 hr. The mixture was cooled to r.t., quenched with water and extracted with excess EtOAc. The combined extracts were dried over a drying agent filtered and the solvent removed under vacuum. The residue was purified by preparative TLC eluting with EtOAc to afford the product, MS: m/z 538.

Aufarbeitung

  1. temperaturethe mixture was heated at 110° C. for 2 hr
  2. temperatureThe mixture was cooled to r.t.
  3. customquenched with water
  4. extractionextracted with excess EtOAc
  5. customThe combined extracts were dried over a drying agent
  6. filtrationfiltered
  7. customthe solvent removed under vacuum
  8. customThe residue was purified by preparative TLC
  9. washeluting with EtOAc
  10. customto afford the product, MS

Quellen und Nachweise

ORD-Eintrag
ord-5b2ee72421e84c96a53e63a90b2cd355
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084156B2

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