Morpholine, hydrochloride (1:1) → HCID 68542503, Verbindung

HRID 1446659

Reaktionsgleichung

Reaktionsgleichung von HRID 1446659
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][C:17](=O)[CH3:18])[CH:11]=3)=[CH:6][C:5]=12.Cl.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([BH3-])#N.[Na+]>CO>[N:21]1([CH:17]([CH3:18])[CH2:16][C:12]2[CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=3)[CH:15]=[CH:14][N:13]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 197884Morpholine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 68544526HCID 68544526, Verbindung

Produkt 1

HCID 68542503HCID 68542503, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve 1-(4-imidazo[1,2-a]pyridin-7-yl-pyridin-2-yl)-propan-2-one (3.9 g, 15.5 mmol) in methanol (400 mL) under nitrogen. Add morpholine hydrochloride (38.4 g, 20 equiv.) followed by 3 {acute over (Å)} Sieves (7.8 g, powdered and dried in a vacuum oven at 100° C. overnight). Stir five minutes then add sodium cyanoborohydride (1.0 M in THF, 28 mL, 1.8 equiv.) via syringe and stir at room temperature for 5 days. Filter to remove insoluble material, washing with methanol. Concentrate to dryness then make basic with 20% NaOH (aq) and extract with ethyl acetate. Wash organics with aqueous saturated sodium chloride then dry over MgSO4. Filter and concentrate then purify by silica gel (Ethyl Acetate→5% Methanol:DCM→10% Methanol:DCM→5% 2M NH3 in methanol:DCM→10% 2 M NH3 in Methanol:DCM) to give product as a tan solid (3.7 g, 74%). MS (ES), m/z 323 (M+1).

Aufarbeitung

  1. customdried in a vacuum oven at 100° C. overnight)
  2. filtrationFilter
  3. customto remove insoluble material
  4. washwashing with methanol
  5. concentrationConcentrate to dryness
  6. extractionextract with ethyl acetate
  7. dry with materialWash organics with aqueous saturated sodium chloride then dry over MgSO4
  8. filtrationFilter
  9. concentrationconcentrate
  10. customthen purify by silica gel (Ethyl Acetate→5% Methanol:DCM→10% Methanol:DCM→5% 2M NH3 in methanol:DCM→10% 2 M NH3 in Methanol:DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c517cdeddc1b4dac838390de425b15d6
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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