Diisopropylethylamine → N-{5-bromo-2-[(pyridin-2-ylcarbonyl)amino]benzyl}pyridine-2-carboxamide

HRID 1786776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786776
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12].C(N(CC)C(C)C)(C)C.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](Cl)=[O:35]>C(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[C:3]([CH:8]=1)[CH2:2][NH:1][C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=1)=[O:35]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 57598296N-[2-(aminomethyl)-4-bromophenyl]pyridine-2-carboxamide

Produkt 1

HCID 11212049N-{5-bromo-2-[(pyridin-2-ylcarbonyl)amino]benzyl}pyridine-2-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 2-3 (0.050 g, 0.16 mmoles) was dissolved in 6 mL of methylene chloride. To the reaction vessel was added (0.06 mL, 0.32 mmoles) of N,N-diisopropylethylamine and (200 mg, 0.32 mmols, 1.49 mmol/gram) followed by the addition of (0.057 g, 0.32 mmol) picolinoyl chloride. The mixture was stirred until complete by TLC. The compound was then filtered and then the solvent was removed and then purified on a mass guided LC/MS to provide 46 mg (70%) of the title compound. 1H NMR (300 MHz, CDCl3): 8.89 ppm (s, 2H), 8.43 ppm (m, 2H), 8.22 ppm (m, 2H), 8.13 ppm (t, J=4 Hz, 1H), 8.0 ppm (s, 1H), 7.81 ppm (m, 2H), 7.41 ppm (m, 1H), 7.2 ppm (m, 2H), 4.22 ppm (d, J=4 Hz, 2H); HRMS calc'd for C19H15BrN4O2 (M+1) 411.0451; Found: 411.0444

Aufarbeitung

  1. filtrationThe compound was then filtered
  2. customthe solvent was removed
  3. custompurified on a mass

Quellen und Nachweise

ORD-Eintrag
ord-583ff380a4bf48fc946d55bf26c23e13
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507836B2

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