Pyridine → N-(4-amino-5-cyano-6-phenylpyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide

HRID 1364532

Reaktionsgleichung

Reaktionsgleichung von HRID 1364532
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([NH2:16])[CH:3]=1.[O:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[CH2:27][C:28](Cl)=[O:29])[CH3:18].N1C=CC=CC=1>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([NH:16][C:28](=[O:29])[CH2:27][C:20]2[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=2[O:17][CH3:18])[CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 596088(2,5-Dimethoxyphenyl)acetyl chlorideHCID 669206084,6-Diamino-2-phenyl-nicotinonitrile

Produkt 1

HCID 66920724N-(4-amino-5-cyano-6-phenylpyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamideAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 50 mg (0.24 mmol) of 4,6-diamino-2-phenyl-nicotinonitrile in 2 mL of CH2Cl2 was added 150 mg (0.70 mmol) of (2,5-dimethoxyphenyl)acetyl chloride (Example 68A), then 100 μL (1.23 mmol) of pyridine. The mixture was stirred at ambient temperature for 10 minutes then the solvent was removed under reduced pressure. The residue was taken up in 10 mL of ethyl acetate, then extracted with 1 M HCl(aq.) (2×5 mL), saturated NaHCO3(aq) (2×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via silica gel chromatography, eluting with 40% ethyl acetate:hexanes to provide 11 mg (12%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.43 (m, 1H), 7.75 (m, 2H), 7.51 (m, 4H), 6.99 (m, 2H), 6.91 (m, 1H), 6.81 (m, 2H), 3.69 (m, 8H); MS (ESI) m/e 389 (M+H)+, 387 (M−H)−.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. extractionextracted with 1 M HCl(aq.) (2×5 mL), saturated NaHCO3(aq) (2×5 mL), and brine (1×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThis was purified via silica gel chromatography
  7. washeluting with 40% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4ceea1b837974e7aa6d452ed54598519
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888374B2

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