[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:40])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:37](O)=[O:38])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.[N:50]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.CN1CCOCC1>CN(C=O)C.O>[C:37]([C:21]1[C:22]2[NH:23][C:24]3[C:29]([C:30]=2[C:18]([C:14]2[C:13]([CH3:40])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:17]=[CH:16][CH:15]=2)=[CH:19][N:20]=1)=[CH:28][CH:27]=[C:26]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[CH:25]=3)(=[O:38])[NH2:50]A homogeneous, burgundy solution of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-morpholino-9H-pyrido[3,4-b] indole-1-carboxylic acid (0.2860 g, 0.533 mmol), ammonium chloride (0.114 g, 2.132 mmol), BOP (0.306 g, 0.693 mmol), DIPEA (0.447 ml, 2.56 mmol) and N-methylmorpholine (0.229 ml, 2.079 mmol) in DMF (Volume: 3.33 ml) was stirred. After 1 hr, water (35 mL) was added and the mixture was stirred at room temperature for 30 min. The precipitate was filtered, washed with water, dried over Drierite to give the desired product (0.274 g, 0.511 mmol, 96% yield) as a tan solid.
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