N-(4-amino-5-cyano-6-isopropoxypyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide → N-[4-amino-5-cyano-6-(2-methoxyethoxy)pyridin-2-yl]-2-(2,5-dimethoxyphenyl)acetamide

HRID 1364521

Reaktionsgleichung

Reaktionsgleichung von HRID 1364521
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH2:12][O:13][CH3:14])[N:5]=[C:4]([NH2:15])[CH:3]=1.NC1C(C#N)=C(OC(C)C)N=C(N[C:30](=[O:42])[CH2:31][C:32]2[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=2[O:40][CH3:41])C=1>N1C=CC=CC=1.C(Cl)Cl.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH2:12][O:13][CH3:14])[N:5]=[C:4]([NH:15][C:30](=[O:42])[CH2:31][C:32]2[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=2[O:40][CH3:41])[CH:3]=1

Komponenten

6

Edukt 2

HCID 11610382N-(4-amino-5-cyano-6-isopropoxypyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamideHCID 669208584,6-Diamino-2-(2-methoxy-ethoxy)-nicotinonitrile

Produkt 1

HCID 11589125N-[4-amino-5-cyano-6-(2-methoxyethoxy)pyridin-2-yl]-2-(2,5-dimethoxyphenyl)acetamideAusbeute 38,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 42 mg (0.20 mmol) of 4,6-diamino-2-(2-methoxy-ethoxy)-nicotinonitrile in 0.2 mL of pyridine and 1 mL of CH2Cl2 was added 75 mg (0.35 mmol) of 2,5-dimethoxyphenylacetyl chloride (Example 60B). The mixture was stirred at ambient temperature for 10 minutes then diluted with 1 mL of water and concentrated under reduced pressure. The residue was dissolved in 1 mL of ethyl acetate, then extracted with water (1×10 mL), 1M HCl(aq.) (2×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to a yellow solid. The residue was recrystallized from 3 mL of ethyl acetate to provide 30 mg (38%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.11 (s, 1H), 7.14 (s, 1H), 6.90 (m, 3H), 6.79 (m, 2H), 4.42 (m, 2H), 3.70 (s, 3H), 3.69 (s, 3H), 3.64 (m, 4H), 3.31 (s, 3H); MS (ESI) m/e=329 (M-CH2CH2OCH3+H)+, 387 (M+H)+, 385 (M−H)−.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 1 mL of ethyl acetate
  3. extractionextracted with water (1×10 mL), 1M HCl(aq.) (2×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid
  7. customThe residue was recrystallized from 3 mL of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-508090874dbb4b69a605ed57bbfd6452
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888374B2

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