Cl.Cl.[NH2:3][C@@H:4]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)[C@H:5]([OH:25])[CH2:6][NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=2)[NH:11][C:10]([CH3:24])([CH3:23])[CH2:9]1.C(N(C(C)C)C(C)C)C.C(Cl)Cl.N1([C:51](=[O:53])[CH3:52])C=CN=C1>>[CH3:23][C:10]1([CH3:24])[CH2:9][C@H:8]([NH:7][CH2:6][C@@H:5]([OH:25])[C@@H:4]([NH:3][C:51](=[O:53])[CH3:52])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=2)[NH:11]1To a solution of (2R,3S)-3-amino-1-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-4-(3-fluorophenyl)butan-2-ol dihydrochloride (0.104 g, 0.379 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.396 ml, 2.27 mmol) in DCM (1.52 ml, 0.379 mmol) was added 1-(1H-imidazol-1-yl)ethanone (0.0396 g, 0.360 mmol) in one portion. The resulting solution was stirred over the weekend. The crude mixture was concentrated and purified with the HPLC. Due to insufficient purity, the title compound was free based and purified with the ISCO MPLC. MS m/z: 470 (M+1).
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