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1,4-Dioxane → 1-(1-(5,6-dimethylpyrazin-2-yl)piperidin-4-yl)-N,N-dimethyl-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

HRID 2382992
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2382992
CC(C)([O-])C.[Na+].O1CCOCC1.[CH3:13][N:14]([CH3:38])[C:15]([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([CH2:31][CH2:30][N:29]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)[CH2:19][CH2:18]1)=[O:16].Cl[C:40]1[N:41]=[C:42]([CH3:47])[C:43]([CH3:46])=[N:44][CH:45]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl.CC#N>[CH3:47][C:42]1[N:41]=[CH:40][C:45]([N:35]2[CH2:36][CH2:37][CH:32]([N:29]3[CH2:28][CH2:27][C:20]4([C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:17]([C:15]([N:14]([CH3:38])[CH3:13])=[O:16])[CH2:18][CH2:19]4)[CH2:31][CH2:30]3)[CH2:33][CH2:34]2)=[N:44][C:43]=1[CH3:46]
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Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 126003905-Chloro-2,3-dimethylpyrazineHCID 23676156Sodium t-butoxideHCID 24798103N,N-dimethyl-1-(piperidin-4-yl)-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

Produkt 1

HCID 236517101-(1-(5,6-dimethylpyrazin-2-yl)piperidin-4-yl)-N,N-dimethyl-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Pd2(dba)3-CHCl3 (5 mg, 0.5 mol %), ligand 1 (8 mg, 2 mol %) and 1.4 eq sodium tert-butoxide (13 mg, 0.14 mmol) were weighed in air and transferred into a microwave tube, followed by dioxane (750 μL), 1.0 eq N,N-dimethyl-1-(piperidin-4-yl)-2′H-spiro[piperidine-4,4′-quinoline]-1′(3′H)-carboxamide (36 mg, 0.10 mmol) and 1.0 eq 5-chloro-2,3-dimethylpyrazine (14 mg). The tube was flushed with nitrogen, capped and stirred at 80° C. for 3 hours. The reaction was cooled to room temperature, diluted with methanol (500 μL), filtered (Whatman 0.45 μm PTFE) and subjected to reverse-phase HPLC purification (2-40% CH3CN gradient [w/0.1% TFA (aq)] over t=10 minutes, 750 μL injected, 35 mL/min) to yield compound no. 20. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 463.4, retention time 2.13 minutes.

Aufarbeitung

  1. customtransferred into a microwave tube
  2. customThe tube was flushed with nitrogen
  3. customcapped
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with methanol (500 μL)
  6. filtrationfiltered (Whatman 0.45 μm PTFE)
  7. customsubjected to reverse-phase HPLC purification (2-40% CH3CN gradient [w/0.1% TFA (aq)] over t=10 minutes, 750 μL injected, 35 mL/min)
  8. customto yield compound no

Quellen und Nachweise

ORD-Eintrag
ord-73f0c82dd4c8472d9903265ffd7f2dc5
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08263605B2

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