Triethylamine → HCID 58486421, Verbindung

HRID 1890770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890770
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:53]=[N:52][C:51]([N:54]3[CH2:59][CH2:58][CH:57]([NH:60][CH3:61])[CH2:56][CH2:55]3)=[C:50]([CH3:62])[C:49]=2[CH3:63])=[CH:44][CH:43]=1.[CH3:64][O:65][C:66]1[CH:84]=[CH:83][C:69]([CH2:70][N:71]2[CH:75]=[C:74]([C:76](O)=[O:77])[C:73]([C:79]([F:82])([F:81])[F:80])=[N:72]2)=[CH:68][CH:67]=1>CN(C=O)C>[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:53]=[N:52][C:51]([N:54]3[CH2:59][CH2:58][CH:57]([N:60]([CH3:61])[C:76]([C:74]4[C:73]([C:79]([F:80])([F:81])[F:82])=[N:72][N:71]([CH2:70][C:69]5[CH:68]=[CH:67][C:66]([O:65][CH3:64])=[CH:84][CH:83]=5)[CH:75]=4)=[O:77])[CH2:56][CH2:55]3)=[C:50]([CH3:62])[C:49]=2[CH3:63])=[CH:44][CH:43]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 582442211-(4-Methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 67368812HCID 67368812, Verbindung

Produkt 1

HCID 58486421HCID 58486421, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Add PyBOP (343 mg, 0.65 mmol) and triethylamine (0.21 mL, 1.50 mmol) to a stirred solution of 1-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)-N-methylpiperidin-4-amine (157 mg, 0.50 mmol) and 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (165 mg, 0.55 mmol) in anhydrous DMF (2.5 mL). Stir the resulting mixture at ambient temperature under N2 overnight. Concentrate, add MeOH, filter solids, and concentrate the filtrate. Dilute the residue with MeOH, and pour onto an SCX column (Thermo Scientific, 10 g). Wash with MeOH, and then elute the product with 2 M NH3/MeOH. Concentrate and purify by flash silica gel chromatography using a gradient of 0 to 10% (10% 2 M NH3/MeOH in EtOAc) in hexanes to obtain the title compound as a white solid (170 mg, 43%). ES/MS m/z 597.0 (M+1).

Aufarbeitung

  1. concentrationConcentrate
  2. additionadd MeOH
  3. filtrationfilter solids
  4. concentrationconcentrate the filtrate
  5. additionDilute the residue with MeOH
  6. additionpour onto an SCX column (Thermo Scientific, 10 g)
  7. washWash with MeOH
  8. washelute the product with 2 M NH3/MeOH
  9. concentrationConcentrate
  10. custompurify by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ba5e918971504885b64f597e5cf52f6b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507490B2

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