N1C=CC=CC=1.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([NH2:16])[CH3:15])[CH:8]=1.[CH:17]1([CH3:29])[CH2:22][CH2:21][CH:20]([CH:23]([CH3:25])[CH3:24])[CH:19]([C:26](Cl)=[O:27])[CH2:18]1>O1CCCC1>[CH:23]([C@@H:20]1[CH2:21][CH2:22][C@@H:17]([CH3:29])[CH2:18][C@H:19]1[C:26]([NH:16][CH:14]([CH3:15])[CH2:13][C:9]1[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=1)=[O:27])([CH3:25])[CH3:24]In a 25 mL round bottom flask, fitted with magnetic stirrer, 15 mL of tetrahydrofuran, 1.5 mmol (1.5 eq.) of pyridine and 1.1 mmol (1.1 eq.) of 1-(pyridin-3-yl)propan-2-amine were added. p-Menthane carboxylic acid chloride (1.0 mmol) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was extracted with MTBE and NaOH (1N in water). The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography, obtaining 220 mg of a white solid, mp 108-110° C.
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