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Diisopropylethylamine → 3-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1'-(5-ethylpyrimidine-2-yl)-1,4'-bipiperidine-2-one

HRID 407898
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 407898
Cl.[F:2][C:3]1[CH:22]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[C:20]([F:27])=[CH:19][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:7]1=[O:18].CCN(C(C)C)C(C)C.Cl[C:38]1[N:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][N:39]=1>CS(C)=O.O.CCOC(C)=O>[F:2][C:3]1[CH:22]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[C:20]([F:27])=[CH:19][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:38]3[N:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][N:39]=3)[CH2:14][CH2:13]2)[C:7]1=[O:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 866880843-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1,4'-bipiperidin-2-one HCl salt

Produkt 1

HCID 761660633-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1'-(5-ethylpyrimidine-2-yl)-1,4'-bipiperidine-2-oneAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1,4′-bipiperidin-2-one HCl salt (64 mg, 0.15 mmol) and DIEA (0.080 mL, 0.45 mmol) in DMSO (2 mL) was added 2-chloro-5-ethylpyrimidine (26 mg, 0.18 mmol). The reaction was heated at 120° C. overnight. The reaction was cooled to ambient temperature and diluted with water (2 mL) and EtOAc (5 mL). The organic layer was separated and the aqueous washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated. The crude residue was purified by reverse phase HPLC (5 to 95% acetonitrile in water with 0.1% TFA). The combined fractions were concentrated to remove CH3CN and the pH adjusted to neutral by the addition of NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were dried with MgSO4 and concentrated to give 3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1′-(5-ethylpyrimidine-2-yl)-1,4′-bipiperidine-2-one (15 mg, 20%) as an off white solid. Mass spectrum (apci) m/z=495.2 (M+H).

Aufarbeitung

  1. temperatureThe reaction was cooled to ambient temperature
  2. customThe organic layer was separated
  3. washthe aqueous washed with EtOAc
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude residue was purified by reverse phase HPLC (5 to 95% acetonitrile in water with 0.1% TFA)
  7. concentrationThe combined fractions were concentrated
  8. customto remove CH3CN
  9. additionneutral by the addition of NaHCO3
  10. extractionThe aqueous layer was extracted with EtOAc
  11. dry with materialThe combined organic layers were dried with MgSO4
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b203ae07997749639149da066fab459c
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754226B2

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