Triethylamine → HCID 68585189, Verbindung

HRID 17477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17477
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:9](N(CC)CC)C.F[C:17]1[C:18]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]2[C:25]=1[O:24][C:23]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)(C)[NH:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]3[C:25]=2[O:24][C:23]([N:27]([CH3:9])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[N:22]3)[CH2:4]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685847727-Fluoro-5-methyl-2-methylpyridin-2-ylamino-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 68585189HCID 68585189, VerbindungAusbeute 26,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

(3S)-3-(Dimethylamino)pyrrolidine (63.2 μl, 0.498 mmol) and triethylamine (81.7 μl, 0.586 mmol) were added to a dimethyl sulfoxide (3 ml) solution of 7-fluoro-5-methyl-2-methylpyridin-2-ylamino-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-189) (105 mg, 0.293 mmol), followed by stirring in an oil bath at 95° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (50 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1), and the obtained eluate was recrystallized from isopropanol to obtain the entitled compound (35.0 mg, 26.4%) as a colorless solid.

Aufarbeitung

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (50 ml)
  4. washwashed with saturated brine (50 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate and concentration
  6. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1)
  7. customthe obtained eluate was recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-f9b627c6ef7c4f7dad3ebeb10f0f4ec0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

Notizen zur Reaktion

Wird geladen…