C(OC([NH:8][C:9]([NH:23]C(OC(C)(C)C)=O)=[N:10][CH:11]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][N:17]=2)[CH2:12]1)=O)(C)(C)C.[ClH:31]>ClCCl.O1CCOCC1>[ClH:31].[ClH:31].[CH3:22][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([N:13]2[CH2:14][CH2:15][CH:11]([NH:10][C:9]([NH2:23])=[NH:8])[CH2:12]2)[CH:21]=1To a solution of N,N′-bis(tert-butoxycarbonyl)-N″-(1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)guanidine (210 mg) in dichloromethane (4 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4N, 4 ml), and the mixture was stirred at ambient temperature for 24 hours. The solvent was evaporated under reduced pressure. To the residue was added 10% methanol in ethyl acetate (50 ml). The resultant precipitate was collected by filtration and dried under reduced pressure to give (1-(4-methylpyridin-2-yl)-pyrrolidin-3-yl)guanidine dihydrochloride (140 mg).
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