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Methanol → 5-methyl-7-[3-(1H-pyrazol-4-ylethynyl)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374956
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2374956
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[N:15]3)=[C:10]([CH3:30])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:31]([C:33]1[CH:34]=[N:35][NH:36][CH:37]=1)#[CH:32].C(N(CC)CC)C.CO>CN(C=O)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH3:30][C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:32]#[C:31][C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)[CH:3]=2)[N:16]2[C:11]=1[CH:12]=[N:13][C:14]([NH:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1)=[N:15]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 112135557-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amineHCID 140415974-Ethynyl-1H-pyrazole

Produkt 1

HCID 587119515-methyl-7-[3-(1H-pyrazol-4-ylethynyl)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 7-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (Example 9) (27 mg, 0.05 mmol) in DMF (1.0 mL) was added 4-ethynyl-1H-pyrazole (6.9 mg, 0.07 mmol), bis(triphenylphosphine)-palladium (II) chloride (4.0 mg, 0.006 mmol), copper (I) iodide (2.0 mg, 0.01 mmol) and triethyl amine (0.06 mL, 0.43 mmol). In a sealed reaction vessel, the mixture was heated with microwave radiation at 150° C. for 20 minutes. After cooling to room temperature, removed solvent under reduced pressure to give an oily residue which was treated with methanol (5 mL) forming a suspension. Filtered solids and washed with ethyl acetate (10 mL) and DMF (1 mL). The combined filtrate was concentrated under reduced pressure and resulting brown oil was dissolved in ethyl acetate (50 mL), washed with 0.1N HCl (3×50 mL), saturated NaHCO3 aqueous solution (2×50 mL) and brine (1×50 mL). Dried over MgSO4, filtered and solvent removed under reduced pressure to give a light brown oil. Dissolved oil in hot ethyl acetate and silica gel (2.0 g) was added followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to isocratic elution using ethyl acetate:hexanes (50:50) followed by ethyl acetate:methanol (85:15) using a Biotage silica gel cartridge (8.0 g). The appropriate fractions were combined and concentrated under reduced pressure to give 5-methyl-7-[3-(1H-pyrazol-4-ylethynyl)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.0053 g) as a tan solid. MS m/z 482 (M+1).

Aufarbeitung

  1. customIn a sealed reaction vessel
  2. temperatureAfter cooling to room temperature
  3. customremoved solvent under reduced pressure
  4. customto give an oily residue which
  5. customforming a suspension
  6. filtrationFiltered solids
  7. washwashed with ethyl acetate (10 mL) and DMF (1 mL)
  8. concentrationThe combined filtrate was concentrated under reduced pressure
  9. customresulting brown oil
  10. washwashed with 0.1N HCl (3×50 mL), saturated NaHCO3 aqueous solution (2×50 mL) and brine (1×50 mL)
  11. dry with materialDried over MgSO4
  12. filtrationfiltered
  13. customsolvent removed under reduced pressure
  14. customto give a light brown oil
  15. additionsilica gel (2.0 g) was added
  16. customfollowed by evaporation of the volatiles under reduced pressure
  17. washsubjected to isocratic elution
  18. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5e52287188024473bdb5e5e224e70c3a
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07462614B2

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