2-Aminoadamantane hydrochloride → 5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

5-Chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (91 mg, 0.4 mmol, CAS#: 128455-63-0, purchased from Maybridge) 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-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (55 mg, 38%). Mass spectrum: m/z: 362.1 (M+1).

1. customthe organic layer was separated
2. extractionThe aqueous layer was extracted twice with dichloromethane
3. customThe combined organic phases were dried under vacuum
4. custompurified by C-18

ORD 기록

ord-568874b6af5e4e4ea6e75104603ebf6e

출처 데이터셋

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07728029B2