Triethylamine → HCID 68650403, Verbindung

HRID 646679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646679
[NH2:1][C:2]1[CH:3]=[N:4][C:5](Br)=[CH:6][N:7]=1.CC[C:11]([NH2:13])=[O:12].[C:14]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)([O:16][CH3:17])=[O:15].[CH2:27](N(CC)CC)[CH3:28]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:22]2[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=2)[C:14]([O:16][CH3:17])=[O:15])=[N:4][C:3]=1[C:11]([NH:13][CH2:27][CH3:28])=[O:12]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 131728097HCID 131728097, Verbindung

Produkt 1

HCID 68650403HCID 68650403, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-6-bromopyrazine-2-ethylcarboxamide (5.0 g, 20.4 mmol), [1,1′bis-(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (0.93 g, 2.04 mmol), 3-carbomethoxyphenylboronic acid (4.4 g, 24.4 mmol) in DMF (30 mL) was de-gassed with nitrogen. Triethylamine (5.7 mL, 40.1 mmol) was then added and the resulting mixture was heated at 85° for 2.5 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL), filtered over silica gel, washed with saturated sodium bicarbonate solution (150 mL), dried over sodium sulfate, filtered, and concentrated. The oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield) to give methyl 3-{5-amino-6-[(ethylamino)carbonyl]pyrazin-2-yl}benzoate (4.3 g, 70% yield): 1H NMR (400 MHz, CDCl3): 8.66 (s, 1H), 8.53-8.52 (t, 1H), 8.08-8.06 (m, 2H), 8.00 (b, 1H), 3.5 (t, 1H), 3.97 (s, 3H), 2.91-2.88 (m, 1H), 0.94-0.85 (m, 2H), 0.72-0.62 (m, 2H); MS (EI) for C15H16N4O3: 301 (MH+).

Aufarbeitung

  1. customwas de-gassed with nitrogen
  2. temperaturethe resulting mixture was heated at 85° for 2.5 hours
  3. filtrationfiltered over silica gel
  4. washwashed with saturated sodium bicarbonate solution (150 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield)

Quellen und Nachweise

ORD-Eintrag
ord-24bd5747960f4881977ab8dfc11619a4
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704995B2

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