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Pyridine → 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

HRID 1011819
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1011819
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:29])[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:20]=[C:21]([O:23][CH:24]([CH2:27][F:28])[CH2:25][F:26])[CH:22]=3)[C:17](O)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[NH2:36][C:37]1[CH:42]=[N:41][C:40]([CH3:43])=[CH:39][N:38]=1>C(Cl)Cl>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:29])[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:20]=[C:21]([O:23][CH:24]([CH2:25][F:26])[CH2:27][F:28])[CH:22]=3)[C:17]([NH:36][C:37]3[CH:42]=[N:41][C:40]([CH3:43])=[CH:39][N:38]=3)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 3132155-Methylpyrazin-2-amineHCID 59127163HCID 59127163, Verbindung

Produkt 1

HCID 536295793-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamideAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

1-Chloro-N,N-2-trimethylpropenylamine (0.08 mL, 0.60 mmol) was added to a solution of 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}benzoic acid (215 mg, 0.5 mmol) in DCM (5 mL) and the reaction stirred at RT for 30-40 minutes. Pyridine (0.08 mL, 1.0 mmol) and 2-amino-5-methylpyrazine (108 mg, 1.0 mmol) were added and the reaction stirred for 16 hours before being concentrated in vacuo and water (20 mL) added. The mixture was extracted with ethyl acetate (3×20 mL), washed with 1N hydrochloric acid (20 mL), a saturated solution of sodium hydrogen carbonate (20 mL), brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0-10% methanol in DCM, to give the desired compound as a white solid (150 mg). 1H NMR δ (CDCl3): 2.40 (quintet, 2H), 2.56 (s, 3H), 4.22-4.31 (m, 2H), 4.32-4.40 (m, 2H), 4.62-4.82 (m, 5H), 7.06 (t, 1H), 7.38 (t, 1H), 7.47 (t, 1H), 8.15 (s, 1H), 8.17 (s, 1H), 8.25 (d, 1H), 8.46 (s, 1H), 9.55 (s, 1H); m/z 518 (M+H)+, 516 (M−H)−

Aufarbeitung

  1. stirringthe reaction stirred for 16 hours
  2. concentrationbefore being concentrated in vacuo and water (20 mL)
  3. additionadded
  4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  5. washwashed with 1N hydrochloric acid (20 mL)
  6. dry with materiala saturated solution of sodium hydrogen carbonate (20 mL), brine (20 mL), dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed on silica
  9. washeluting with a gradient of 0-10% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-683a8464cc814eacb938675b9f3029ef
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07977328B2

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