[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19](O)=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:11]2=3)=[CH:4][CH:3]=1.C[CH2:28][N:29]=C=NCCCN(C)C.Cl.CN.C1COCC1>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([NH:29][CH3:28])=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:11]2=3)=[CH:6][CH:7]=15-(4-Fluoro-phenylethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (20 mg, 0.0044 mmol) was dissolved in DMF and EDCI.HCl (42.17 mg, 0.22 mmol) was added. Methyl amine (2.0 M) in THF (0.0446 mL, 0.0089 mmol) was added. The reaction mixture was stirred at RT overnight. The progress of reaction was monitored by TLC and LCMS. The DMF was evaporated under vacuum and the product purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.05 (s, 1H), 7.82 (d, 1H), 7.62 (m, 3H), 7.20 (t, 2H), 4.40 (m, 1H), 3.70 (m, 1H), 3.38 (m, 4H), 3.20 (s, 3H), 2.90 (s, 3H).
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