[C:1]([C:4]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][N:8]2[C:19](=[O:36])[C@@H:20]([NH:28]C(=O)OC(C)(C)C)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C@@H:20]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:19]([N:8]1[C:9]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:12]=[C:4]([C:1]([NH2:2])=[O:3])[C:5]=2[CH2:6][CH2:7]1)=[O:36]To a 20 ml vial was added crude (S)-tert-butyl 1-(4-carbamoyl-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 60.B (75 mg, 0.1 mmole), 20 ml of DCM and 10 ml of TFA. The reaction was stirred at room temperature for 12 hours at which time the crude was partitioned between 600 ml DCM and 100 ml saturated sodium carbonate. The organic layer was extracted once more with 100 ml of water, the organic layer dried with sodium sulfate and the solvent removed to give (S)-1-(2-amino-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxamide 60.0 as an off white solid. (49 mg, 82% yield).
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