Pyridine → HCID 178489755, Verbindung

HRID 1911299

Reaktionsgleichung

Reaktionsgleichung von HRID 1911299
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[N:15](C(OC(C)(C)C)=O)[N:14]=[C:13]([CH2:23][CH2:24][C:25]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH3:34])[CH:26]=2)[CH:12]=1.N1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:32][O:31][C:29]1[CH:30]=[C:25]([CH2:24][CH2:23][C:13]2[CH:12]=[C:11]([NH:10][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH:15][N:14]=2)[CH:26]=[C:27]([O:33][CH3:34])[CH:28]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 7412Benzoyl chlorideHCID 57440371Tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate

Produkt 1

HCID 178489755HCID 178489755, VerbindungAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Benzoyl chloride (56 μl, 0.47 mmol, 1.1 eq) was added dropwise to a mixture of tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate (150 mg, 0.43 mmol, 1 eq) and pyridine (104 μl, 1.29 mmol, 3 eq) in DCM (1.5 ml) at ambient temperature. After stirring at ambient temperature for 2 h, a solution of TFA (321 μl, 4.32 mmol, 10 eq) in DCM (2.7 ml) was added dropwise and stirring was continued for a further 1 h. The reaction mixture was concentrated and the crude product was purified by reverse-phase prep. HPLC (basic) using a 33-53% gradient of acetonitrile in water containing 1% ammonium hydroxide solution. The clean fractions were taken and evaporated to afford the title compound as a colourless foamy solid (100 mg, 66% yield).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a further 1 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was purified by reverse-phase prep
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9246c0858b034098b7c4f67d36f3bbe0
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604022B2

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