Ethyl 6-(2-(tert-butoxycarbonyl-(isopropyl)amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate → Ethyl 6-(2-(isopropylamino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate
Reaction equation
C(OC([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[CH:34]([NH:8][C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)([CH3:35])[CH3:36]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 6-(2-(tert-butoxycarbonyl-(isopropyl)amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate (75 mg) in 4 ml of TFA was stirred at room temperature for 2 hours. The solvent was evaporated and the residue was purified by column chromatography on silica gel using ethyl acetate/hexane (50-100%) as eluent to give 50 mg of ethyl 6-(2-(isopropylamino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate as a light yellow solid. LCMS (Conditions C): 2.90 min (RT); (M+H)+=407.33 (100%). 1H NMR, 400 MHz, CDCl3: δ 8.25 (s, 1 H), 8.16 (m, 1 H), 8.02 (m, 2 H), 7.52-7.43 (m, 3 H), 7.37 (d, 1H), 7.29 (s, 1H), 4.44 (q, J=7.1 Hz, 2 H), 3.60 (m, 1 H), 1.42 (m, 9 H).
Workup
- customThe solvent was evaporated
- customthe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-11559560ed1f42d3aa5a82cd51c9b534
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338604B2
Reaction notes
Loading…