Trifluoroacetic acid → Alogliptin Impurity D
Reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12]C(=O)OC(C)(C)C)[CH2:7]1)#[N:2].C(O)(C(F)(F)F)=O>>[NH2:12][C@@H:8]1[CH2:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]2[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=2[C:1]#[N:2])[CH2:7]1Participants
3
Procedure
To a microwave vial equipped with a stir bar was added tert-butyl [(3R)-1-(2-cyanobenzyl)piperidin-3-yl]carbamate (1000 mg, 3.17 mmol) and TFA (1000 μl, 12.98 mmol). The reaction was stirred at room temperature for 30 minutes. The LCMS taken after 30 minutes indicates formation of the desired product. The crude reaction mixture was concentrated in vacuo, and was then dissolved in ethyl acetate and filtered through a sodium bicarbonate filter. The combined organics were concentrated under reduced pressure. The material was dissolved in acetonitrile and water, and was dried on the lyophilizer overnight.
Workup
- customTo a microwave vial equipped with a stir bar
- waitThe LCMS taken after 30 minutes