Triethylamine → HCID 67113434, Verbindung

HRID 2088904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088904
Cl[C:2]1[C:3]2[C@H:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:14][C:15]([F:35])([F:34])[C:16]1[N:17]=[C:18]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[N:19]([CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:20]=1.C(N(CC)CC)C>CN1CCCC1=O>[CH3:12][C@H:11]1[C:3]2[C:2]([N:31]3[CH2:30][CH2:29][CH:28]([C:18]4[N:19]([CH2:21][CH2:22][N:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[CH:20]=[C:16]([C:15]([F:34])([F:35])[F:14])[N:17]=4)[CH2:33][CH2:32]3)=[N:7][CH:6]=[N:5][C:4]=2[NH:8][C:9](=[O:13])[CH2:10]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67113455HCID 67113455, VerbindungHCID 86666575(R)-4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one

Produkt 1

HCID 67113434HCID 67113434, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Add (R)-4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (28.30 g, 143.20 mmol), 4-(4-trifluoromethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine (49.83 g, 1.10 eq) and triethylamine (43.47 g, 3.0 eq) in N-methylpyrrolidinone (86 mL). Heat the reaction mixture to 130° C. Cool the reaction mixture to room temperature after 2 hours. Pour the reaction mixture over ice/water (500 mL) with stirring. Extract with ethyl acetate (4×200 mL). Wash the organics with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate and concentrate in vacuo. Suspend the solid in hexanes and stir for 30 minutes. Filter and dry under vacuum. Add 75% methyl tert-butyl ether in hexanes (800 mL) and heat to reflux. Cool the mixture to room temperature. Filter, wash with 75% methyl tert-butyl ether in hexanes (200 mL), and dry under vacuum at 40° C. to give the title compound (48.00 g, 70%). MS (ES) m/z=478 [M]+.

Aufarbeitung

  1. temperatureCool the reaction mixture to room temperature after 2 hours
  2. extractionExtract with ethyl acetate (4×200 mL)
  3. washWash the organics with saturated aqueous sodium chloride solution
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate in vacuo
  6. stirringstir for 30 minutes
  7. filtrationFilter
  8. customdry under vacuum
  9. additionAdd 75% methyl tert-butyl ether in hexanes (800 mL)
  10. temperatureheat to reflux
  11. temperatureCool the mixture to room temperature
  12. filtrationFilter
  13. washwash with 75% methyl tert-butyl ether in hexanes (200 mL)
  14. customdry under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-1cb6f4c501f345a69c01504da928ee39
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436002B2

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