Reaktion #41109

Reaktionsgleichung

DIPEA

TSTU

5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid

2-aminoadamantane hydrochloride

→

5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Ausbeute 60.0%

Lösungsmittel

water

dichloromethane

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic layer was separated
2. 2
   ExtraktionThe aqueous layer was extracted twice with dichloromethane
3. 3
   SonstigeThe combined organic phases were dried under vacuum
4. 4
   Sonstigepurified by C-18

Vorschrift

5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid (64 mg, 0.4 mmol, CAS#: 54367-66-7, purchased from Oakwood) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.28 mL, 1.6 mmol) and TSTU (145 mg, 0.44 mmol) were added to the above mixture. After the mixture was stirred for 1 h, the appearance of active ester was detected by LC-MS. Then 2-aminoadamantane hydrochloride (75 mg, 0.4 mmol) was added. After another 2 hours water was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane. The combined organic phases were dried under vacuum and purified by C-18 reversed phase HPLC with a gradient of 10-100% acetonitrile/water to give 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (70 mg, 60%). Mass spectrum: m/z: 294.1 (M+1).

Quelle