4,5-dihydro-1H-imidazol-2-ylamine tosylate → 2-amino-5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)benzamide

反応式

S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH:12]1[CH2:16][CH2:15][N:14]=[C:13]1[NH2:17].[Na].C(NC(C=C([C:29]1[C:30]([NH2:39])=[C:31]([CH:35]=[C:36]([Br:38])[CH:37]=1)[C:32]([O-])=[O:33])C)=O)(C)(C)C>CC(O)C>[NH2:39][C:30]1[CH:29]=[CH:37][C:36]([Br:38])=[CH:35][C:31]=1[C:32]([NH:17][C:13]1[NH:14][CH2:15][CH2:16][N:12]=1)=[O:33]

参加物

実験手順

A mixture of 4,5-dihydro-1H-imidazol-2-ylamine tosylate (0.523 g; 2.03 mmol) and sodium (37 mg; 1.63 mmol) in 2-propanol (16 ml) is refluxed for 30 min. 1-(tert-Butylcarbamoyl)-prop-1-en-2-yl-2-amino-5-bromobenzoate (example 15) (0.300 g; 0.812 mmol) is added and the mixture is refluxed over night. The precipitate formed is filtered off and discarded. The filtrate is evaporated, and the residue is purified by preparative RP-HPLC (column: Xbridge C18 (Waters); water-ACN; modifier: ammonia) to yield the title compound (C10H11BrN4O).