4-Hydroxypyrrolidine → 1-tert-butyl-5-(3-hydroxy-pyrrolidin-1-yl)-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide
Reaction equation
[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[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25]1>CN1CCCC1=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[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25]1)=[O:13])[CH2:8]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 36, 101 mg; 0.30 mmol) and pyrrolidin-3-ol (+/−) (0.25 mL; 3.0 mmol) in N-methylpyrrolidinone (1 mL) was heated to 250° C. in a sealed vial under microwave irradiation for 4 hr. The mixture was allowed to cool to room temperature and the crude product was purified by reverse phase HPLC to provide 1-tert-butyl-5-(3-hydroxy-pyrrolidin-1-yl)-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (25 mg, 22%) as an off white solid. ES-HRMS m/e calcd for C22H35N4O2 (M+H+) 358.2602, found 358.2602.