Pyrazole → 2'-tert-butyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid adamantan-2-ylamide

HRID 12853

Reaktionsgleichung

Reaktionsgleichung von HRID 12853
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1Cl)=[O:13])[CH2:8]2.[NH:24]1[CH:28]=[CH:27][CH:26]=[N:25]1.[F-].[K+]>CS(C)=O>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[N:24]1[CH:28]=[CH:27][CH:26]=[N:25]1)=[O:13])[CH2:8]2

Komponenten

5

Edukt 3

HCID 1048PyrazoleHCID 522689Potassium FluorideHCID 250144171-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Produkt 1

HCID 167425402'-tert-butyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid adamantan-2-ylamideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

In a Personal Chemistry microwave process tube (Biotage AB, Sweden), 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 36, 100 mg, 0.30 mmol), pyrazole (41 mg, 0.60 mmol), KF (35 mg, 0.60 mmol) and DMSO (2 mL) were well mixed. The tube was sealed with a septum and was submitted to 150 W microwave irradiation using a Personal Chemistry Microwave Synthesis system (Biotage AB, Sweden) at 230° C. for 20 minutes. The reaction mixture was partitioned between ethyl acetate and water and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, concentrated in vacuo and purified by C-18 reversed phase prep-HPLC with a gradient of 10-100% acetonitrile/water to give 2′-tert-butyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid adamantan-2-ylamide (45 mg, 41%). Mass spectrum: m/z: 368.2 (M+1).

Aufarbeitung

  1. customThe tube was sealed with a septum
  2. customwas submitted to 150 W microwave irradiation
  3. customa Personal Chemistry Microwave Synthesis system (Biotage AB, Sweden) at 230° C. for 20 minutes
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. extractionthe aqueous phase was extracted three times with ethyl acetate
  6. concentrationconcentrated in vacuo
  7. custompurified by C-18

Quellen und Nachweise

ORD-Eintrag
ord-c38d0564c8994c85877cb4441405fdcf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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