Triethylamine → Ethyl-4-cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

HRID 17368

Reaktionsgleichung

Reaktionsgleichung von HRID 17368
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:14](F)=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[C:11]([C:23]#[N:24])[C:9]=2[N:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([N:36]3[CH2:37][CH2:38][C@H:34]([N:33]([CH3:39])[CH3:32])[CH2:35]3)=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[C:11]([C:23]#[N:24])[C:9]=2[N:10]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

Produkt 1

HCID 51041664Ethyl-4-cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylateAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Ethyl-4-cyan-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate 111) (200 mg, 0.62 mmol) was dissolved in dimethyl sulfoxide (12 ml), and at room temperature, triethylamine (112 μl, 0.80 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (94 μl, 0.74 mmol) dissolved in dimethyl sulfoxide (2 ml) was added all at a time, followed by further stirring for 1 hour. The mixture liquid was cooled to room temperature, then this was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, this was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=98:2) to obtain the entitled compound (17.5 mg, 7%) as a yellow powdery crystal.

Aufarbeitung

  1. additionwas added all at a time
  2. temperatureThe mixture liquid was cooled to room temperature
  3. customThe aqueous layer was separated
  4. extractionthis was extracted twice with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe solvent was evaporated away
  9. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=98:2)

Quellen und Nachweise

ORD-Eintrag
ord-f2015a023d4a485db0465b7f7b524891
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

Verknüpfte Notizen

Wird geladen…