CCN(C(C)C)C(C)C.[N:10]1([C:15]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=2)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([O:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=2)[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[O:51]=[C:50]([N:52]1[CH2:53][CH2:54][CH:55]([O:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:66])[F:67])[CH:60]=2)[CH2:56][CH2:57]1)[CH2:49][NH:48][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[O:16])=[CH:25][CH:24]=1DIPEA (200 mg, 1.5 mmol) was added to a stirred solution of 4-(pyrrolidine-1-carbonyl)-benzoic acid (75 g, 0.34 mmol) in DMF (5 mL) followed by HOBt (50 mg, 0.37 mmol) and EDCI (164 mg, 0.85 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (127 mg, 0.37 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected to afford 130 mg (75.58% Yield) of N-{2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-4-(pyrrolidine-1-carbonyl)-benzamide. LC/MS [M+H]+: 504, 94.9%. 1H NMR (300 MHz, DMSO-d6): δ 7.2 (t, 1H), 7.96 (d, 2H), 7.64-7.48 (m, 3H), 7.36 (t, 3H), 4.9 (b, 1H), 4.2 (d, 2H), 4.0 (d, 2H), 3.5 (t, 2H), 3.4 (t, 2H), 2.1-1.8 (m, 6H), 1.7 (m, 3H).
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