Triethylamine → 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide

HRID 1514989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514989
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36].C(N(CC)CC)C.N[C:46]1[CH:47]=[C:48]([CH3:55])[C:49](C)([CH3:53])[NH:50][C:51]=1C>CN(C=O)C>[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:2][C:51]2[CH:46]=[CH:47][C:48]([CH3:55])=[C:49]([CH3:53])[N:50]=2)=[O:32])=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669662025-Amino-2,3-dimethyllutidine

Produkt 1

HCID 669660594-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To DMF (20 mL) were added HATU (2.87 g, 7.55 mmol), 4-amino-3-nitrobenzoic acid (916 mg, 5.03 mmol), triethylamine (1.05 mL, 762 mmol) and 5-amino-2,3-dimethyllutidine (615 mg, 5.03 mmol) [J. Het. Chem. 31, 1641 (1994)]. The mixture was stirred at ambient temperature for 1 h, then at 80° C. for 18 h. The solution was decanted into ethyl acetate and extracted once with water and five times with brine, then dried, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography using a gradient of 80-100% heptane/ethyl acetate to give 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide. MS (m/z) 287.0 (M+1).

Aufarbeitung

  1. waitat 80° C. for 18 h
  2. customThe solution was decanted into ethyl acetate
  3. extractionextracted once with water and five times with brine
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ef9ed8c2983408895d88b71b23fcab6
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

Notizen zur Reaktion

Wird geladen…