Trifluoroacetic acid → HCID 57461728, compound
Reaction equation
C(O)(C(F)(F)F)=O.[C:8]1([C:14]2[N:15]=[CH:16][N:17]([CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)[C:18]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[C:8]1([C:14]2[N:15]=[CH:16][N:17]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:18]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
TFA (2 mL) was added to a solution of tert-butyl 4-(4-phenyl-5-pyrimidin-4-yl-1H-imidazol-1-yl)piperidine-1-carboxylate (C22) (267 mg, 0.658 mmol) in dichloromethane (5 mL). After 2 hours, the reaction was concentrated in vacuo, and then treated with saturated aqueous sodium bicarbonate solution. The mixture was extracted with warm ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting light yellow oil solidified over the course of several days to provide 105 mg of product that was contaminated with approximately 20% of a related impurity. Fine white needles precipitated out of the aqueous layer; these were collected by filtration to provide additional product as a cream colored solid. Yield from aqueous layer: 54 mg, 0.18 mmol, 27%. 1H NMR (400 MHz, CDCl3) δ 1.83-1.93 (m, 2H), 2.12-2.18 (m, 2H), 2.72 (ddd, J=12.3, 12.3, 2.3 Hz, 2H), 3.20-3.25 (m, 2H), 4.85 (tt, J=12.0, 4.0 Hz, 1H), 7.19 (dd, J=5.3, 1.5 Hz, 1H), 7.30-7.36 (m, 3H), 7.42-7.45 (m, 2H), 7.85 (s, 1H), 8.54 (d, J=5.4 Hz, 1H), 9.30 (d, J=1.4 Hz, 1H).