[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([C:12]([OH:14])=O)=[CH:7][CH:8]=2)[N:3]=1.[CH:16]([NH2:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl>CC#N.O>[CH:16]([NH:19][C:12]([C:6]1[C:5]([CH3:15])=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)=[O:14])([CH3:18])[CH3:17]A mixture of 2,8-dimethylquinoline-7-carboxylic acid (0.20 g, 0.994 mmol), isopropylamine (0.102 mL, 1.19 mmol) and HATU (0.491 g, 1.29 mmol) in anhydrous MeCN (5 mL) under a nitrogen atmosphere was cooled to 0° C. in an ice bath. To the cooled mixture was added dropwise DIEA (0.69 mL, 3.98 mmol) and the resulting mixture stirred at ambient temperature for 18 hours. The mixture was diluted with water, neutralized with aqueous 1N HCl and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (Biotage SP4, 25M C-18, 5-60% MeCN—H2O) to afford N-isopropyl-2,8-dimethylquinoline-7-carboxamide (0.223 g, 93%).
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