1-(1,3-Dioxolan-2-yl)methanamine → 1-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamine
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].Cl[CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]2[CH:22]=1>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:14][N:13]2[CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a DCM 5 mL solution of 1-(1,3-dioxolan-2-yl)methanamine (814 mg, 7.89 mmol) was added 2-(chloromethyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Intermediate 19) (620 mg, 2.63 mmol). After heating to reflux for 1.5 hr, the reaction mixture (suspension) was cooled to room temperature and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM) to give the title compound as solid (450 mg). LC/MS: m/z 302(M+H).