Pyridine → HCID 178440950, Verbindung

HRID 1072000

Reaktionsgleichung

Reaktionsgleichung von HRID 1072000
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:13]1[CH:18]=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25]C=1)=[O:21].C(N(C(C)C)CC)(C)C.C[N:42]([CH:44]=[O:45])C>C(Cl)Cl.CO>[C:44]([OH:45])(=[O:10])[C:20]([OH:22])=[O:21].[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:44]([N:42]2[CH2:23][CH2:28][C:27]3[NH:13][CH:18]=[N:29][C:26]=3[CH2:25]2)=[O:45])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 134164-tert-Butylbenzyl alcoholHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Produkt 1

HCID 178440950HCID 178440950, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-tert-butylbenzyl alcohol (1.97 g, 12 mmol) in DCM (30 mL) was added pyridine (1.3 mL) and then a solution of 4-nitrophenyl chloroformate (1.57 g, 7.8 mmol) in DCM (20 mL). The mixture was stirred at room temperature for 1 h, concentrated under reduced pressure, and to the residue was added a mixture of of 4,5,6,7-tetrahydromidazo[4,5-c]pyridine (1.5 g, 7 mmol), methanol (3.3 mL), DMF (30 mL), and diisopropylethylamine (4.1 mL). The resulting mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was distributed between water and ethyl acetate, phases were separated, and the organic layer was washed with water, dried (MgSO4), and filtered. A solution of oxalic acid (0.63 g) in ethyl acetate was added to the filtrate and the mixture was allowed to stand for 24 h. Filtration yielded the title compound as colorless solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionto the residue was added
  3. stirringThe resulting mixture was stirred at room temperature overnight
  4. concentrationconcentrated under reduced pressure
  5. customwere separated
  6. washthe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. additionA solution of oxalic acid (0.63 g) in ethyl acetate was added to the filtrate
  10. waitto stand for 24 h
  11. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-597b2f8d88f84ce8a7442fc7e07d1de4
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908926B1

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