Triethylamine → 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile

HRID 549239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549239
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([N:17]1[C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:20][C:19]([C:29]([NH2:31])=O)=[N:18]1)[CH2:15][CH3:16].C(N(CC)CC)C>ClCCl>[CH2:14]([N:17]1[C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:20][C:19]([C:29]#[N:31])=[N:18]1)[CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 671577891-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide

Produkt 1

HCID 671577501-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrileAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of trifluoroacetic anhydride (2.50 mL, 17.7 mmol) in dichloromethane (32 mL) was added over a period of ten minutes to a 0° C. solution of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide (4.05 g, 16.1 mmol) and triethylamine (4.89 g, 48.3 mmol) in dichloromethane (32 mL). After the addition was complete, the cooling bath was removed and the solution was stirred for three hours. The solution was washed with 2 M aqueous sodium carbonate. The aqueous layer was extracted three times with tert-butyl methyl ether. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (eluting with 40% to 70% ethyl acetate in hexane) to provide 3.98 g of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile as a pale yellow oil.

Aufarbeitung

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. washThe solution was washed with 2 M aqueous sodium carbonate
  4. extractionThe aqueous layer was extracted three times with tert-butyl methyl ether
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by automated flash chromatography (eluting with 40% to 70% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-06267feec9794738995cf08950a373d3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943636B2

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