[CH:1]1([CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=2)[CH2:3][CH2:2]1.[C:19]([N:27]=C=O)(=[O:26])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:1]1([CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:19]([NH2:27])=[O:26])[CH:7]=2)[CH2:3][CH2:2]1
The crude 4-(2-cyclopropyl-2-phenyl-ethyl)-pyridin-2-ylamine (70 mg) is dissolved in methylene chloride (2 mL). Then benzoyl isocynate (86 mg, 0.59 mmol) is added. The reaction mixture is sealed and heated at 50° C. for 16 hour. The solvent is then carefully removed and to the residue are added ethanol (2 mL) and potassium carbonate (61 mg, 0.44 mmol). The resulting mixture is heated at 85° C. for 45 min. Then solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×40 mL). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) followed by Gilson preparative HPLC affords 8 mg of the titled product.
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