Ammonia → 4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:26])[CH2:13][CH2:12]1.N>O>[O:26]=[C:18]1[NH:19][C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[N:17]1[CH:14]1[CH2:15][CH2:16][N:11]([C:2]2[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:13]1

Participants

Procedure

0.50 g (2.4 mmol) 2-bromopyridine-4-carboxylic acid and 1.1 g (5.0 mmol) 1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one were mixed and melted for 10 min using the hot air blower. The reaction mixture was cooled, mixed with water and made basic with ammonia. It was extracted with EtOAc. The aqueous phase was concentrated and purified by HPLC. The product-containing fractions were combined and concentrated to dryness by rotary evaporation.