1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59322396, Verbindung

HRID 1685205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685205
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]([CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11].Cl[C:31]1[C:32]2[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:33]=2[N:34]=[CH:35][N:36]=1.N12CCCN=C1CCCCC2>CC(O)C>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:24]3[CH2:25][CH2:26][N:27]([C:31]4[C:32]5[C:39]([CH3:40])([CH3:41])[C:38](=[O:42])[NH:37][C:33]=5[N:34]=[CH:35][N:36]=4)[CH2:28][CH2:29]3)[N:15]([CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67265197HCID 67265197, VerbindungHCID 86641620HCID 86641620, Verbindung

Produkt 1

HCID 59322396HCID 59322396, VerbindungAusbeute 13,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Combine 4-[4-(3-Chloro-4-fluoro-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl]-piperidine tris hydrochloride (0.3 g; 0.00062 mol), 4-chloro-5,5-dimethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.16 g; 0.0008 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.76 mL; 0.0051 mol) into IPA (10 mL) and stir at 120° C. for 16 h; cool and concentrate. Quench the reaction with saturated sodium bicarbonate solution and extract with EA. Evaporate the EA layer and purify by column chromatography using 0-5% MeOH/DCM as eluent to afford the title compound (0.045 g; 13.5%). MS (ES+): m/z=538 (M+1).

Aufarbeitung

  1. temperaturecool
  2. concentrationconcentrate
  3. customQuench
  4. customthe reaction with saturated sodium bicarbonate solution
  5. extractionextract with EA
  6. customEvaporate the EA layer
  7. custompurify by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a9989efe2b80445c808738b186a31316
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148387B2

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