Potassium Carbonate → HCID 68379922, Verbindung

HRID 2178649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2178649
C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:8][C:9]1[N:10]=[CH:11][N:12]([C:14]2[C:19](=[O:20])[NH:18][C:17]([C:21]([OH:23])=O)=[CH:16][CH:15]=2)[CH:13]=1.Cl.[Cl:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30]Cl.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[Cl:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][N:18]2[C:19](=[O:20])[C:14]([N:12]3[CH:13]=[C:9]([CH3:8])[N:10]=[CH:11]3)=[CH:15][CH:16]=[C:17]2[C:21]1=[O:23]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68380187HCID 68380187, Verbindung

Produkt 1

HCID 68379922HCID 68379922, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (195.4 g, 1414 mmol) was added to a mixture of 5-(4-methyl-1H-imidazol-1-yl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid, hydrochloride salt (C3) (34.5 g, 135 mmol) and 2-chloro-N-(2-chloroethyl)ethanamine hydrochloride (37.8 g, 212 mmol) in N,N-dimethylformamide (670 mL), and the reaction was stirred for 10 minutes. O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 83.5 g, 219 mmol) was added and stirring was continued for an additional 3 hours and 40 minutes. The reaction mixture was then poured into water (4 L) and stirred for 30 minutes. After extraction with dichloromethane (3×1 L), the combined organic layers were washed with saturated aqueous sodium chloride solution (3×3 L), dried over magnesium sulfate, filtered and concentrated in vacuo. Finally, most of the DMF was removed by using a methanol/liquid nitrogen cooler. The residue was stirred in ethyl acetate (approximately 50 mL) for 30 minutes. The solids were collected by filtration and washed with ethyl acetate and pentane, providing the title compound as a yellow solid. Yield: 23.0 g, 75.0 mmol, 56%. LCMS m/z 307.1 (M+1). 1H-NMR (300 MHz, CDCl3) δ 2.29 (br s, 3H), 3.80-3.93 (m, 6H), 4.38-4.44 (m, 2H), 7.13-7.16 (m, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.45 (d, J=7.6 Hz, 1H), 8.24 (d, J=1.0 Hz, 1H).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for an additional 3 hours and 40 minutes
  3. stirringstirred for 30 minutes
  4. extractionAfter extraction with dichloromethane (3×1 L)
  5. washthe combined organic layers were washed with saturated aqueous sodium chloride solution (3×3 L)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customFinally, most of the DMF was removed
  10. stirringThe residue was stirred in ethyl acetate (approximately 50 mL) for 30 minutes
  11. filtrationThe solids were collected by filtration
  12. washwashed with ethyl acetate and pentane

Quellen und Nachweise

ORD-Eintrag
ord-c687af600a6d4d3fa4be92ccdc629d8d
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067934B2

Notizen zur Reaktion

Wird geladen…