Triethylamine → HCID 68586047, Verbindung

HRID 17475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17475
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(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]([N:26]1[CH2:31][CH2:30][N:29]([CH3:32])[C:28](=[O:33])[CH2:27]1)=[N: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:26]2[CH2:31][CH2:30][N:29]([CH3:32])[C:28](=[O:33])[CH2:27]2)=[N:22]3)[CH2:4]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685845617-Fluoro-5-methyl-2-(4-methyl-3-oxopiperazin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 68586047HCID 68586047, VerbindungAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

(3S)-3-(Dimethylamino)pyrrolidine (67.9 μl, 0.535 mmol) and triethylamine (86.1 μl, 0.618 mmol) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-5-methyl-2-(4-methyl-3-oxopiperazin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-188) (150 mg, 0.412 mmol), followed by stirring in an oil bath at 130° C. for 3 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=10:1) to obtain the entitled compound (109 mg, 54.5%) as a colorless foamy substance.

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=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-c139d2a759cd4972aa16659e114b7afb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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