Pyridine → HCID 178491584, Verbindung

HRID 16728

Reaktionsgleichung

Reaktionsgleichung von HRID 16728
ClC(N(C)C)=C(C)C.[CH3:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.[NH2:20][C:21]1[N:25](C(OC(C)(C)C)=O)[N:24]=[C:23]([CH2:33][CH2:34][C:35]2[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[C:37]([O:43][CH3:44])[CH:36]=2)[CH:22]=1.N1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:42][O:41][C:39]1[CH:40]=[C:35]([CH2:34][CH2:33][C:23]2[CH:22]=[C:21]([NH:20][C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:19][CH:18]=3)[NH:25][N:24]=2)[CH:36]=[C:37]([O:43][CH3:44])[CH:38]=1

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 74784-Methoxybenzoic AcidHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 57440371Tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate

Produkt 1

HCID 178491584HCID 178491584, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (89 μl, 0.63 mmol, 1.05 eq) was added dropwise to 4-methoxybenzoic acid (97 mg, 0.63 mmol, 1 eq) in DCM (1.5 ml) at ambient temperature. After stirring at ambient temperature for 1.5 h, a solution of tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate (199 mg, 0.57 mmol, 0.9 eq) and pyridine (142 μL, 1.74 mmol, 2.75 eq) in DCM (2 ml) was added to the reaction mixture and stirring was continued at ambient temperature for a further 3 h. A solution of TFA (386 μL, 5.2 mmol, 8.25 eq) in DCM (3.5 ml) was then added and stirring was continued at ambient temperature for 18 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 (113 mg, 52% yield).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at ambient temperature for a further 3 h
  3. stirringstirring
  4. waitwas continued at ambient temperature for 18 h
  5. concentrationThe reaction mixture was concentrated
  6. customthe crude product was purified by reverse-phase prep
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-032c9e4210a846618db6861409b07b37
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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