Dimethylformamide → (2S,4S)-N-[2-(4-Cinnamylpiperazin-1-yl)ethyl]-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide

HRID 373504

Reaktionsgleichung

Reaktionsgleichung von HRID 373504
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5]1.C1CCN2C(=NCCC2)CC1.CN(C)C=O.[F:35][C:36]1[CH:37]=[C:38]2[C@:45]3([C:49](=[O:50])[NH:48][C:47](=[O:51])[NH:46]3)[CH2:44][C@@H:43]([C:52](Cl)=[O:53])[O:42][C:39]2=[CH:40][CH:41]=1>>[CH2:10]([N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:52]([C@@H:43]2[CH2:44][C@@:45]3([C:49](=[O:50])[NH:48][C:47](=[O:51])[NH:46]3)[C:38]3[C:39](=[CH:40][CH:41]=[C:36]([F:35])[CH:37]=3)[O:42]2)=[O:53])[CH2:5][CH2:6]1)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 541859284-(2-Aminoethyl)-1-cinnamylpiperazineHCID 57210646(2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride

Produkt 1

HCID 57147314(2S,4S)-N-[2-(4-Cinnamylpiperazin-1-yl)ethyl]-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamideAusbeute 92,9 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a chilled mixture (less than -5° C.) of 4-(2-aminoethyl)-1-cinnamylpiperazine (10.0 g, 40.8 mmol), 1,8-diazabicyclo[5,4,0]-7-undecene (6.20 g, 40.8 mmol) and N,N-dimethylformamide (55.0 ml, 710 mmol) was added over 30 minutes a solution of (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride (Reference Example 1, 11.1 g, 37.1 mmol) in N,N-dimethylformamide (100.1 ml, 1.29 mol). After stirring the mixture for 15 hours at 25° C., the solvent was evaporated. The residue was chromatographed on silica gel, eluted with a mixture of AcOEtAcOEt/MeOH (9:1), and evaporated in vacuo to dryness to give a colorless oil of the desired compound (17.5 g, 92.6%).

Aufarbeitung

  1. customthe solvent was evaporated
  2. customThe residue was chromatographed on silica gel
  3. washeluted with a mixture of AcOEtAcOEt/MeOH (9:1)
  4. customevaporated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ac134bcc6a2e48e185503fa2a5bf72a0
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164391

Verknüpfte Notizen

Wird geladen…