Trifluoroacetic acid → Alogliptin Impurity D

HRID 1467305Notes

Reaction equation

HRID 1467305 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]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70652603tert-Butyl (R)-(1-(2-cyanobenzyl)piperidin-3-yl)carbamate

Product 1

HCID 70652209Alogliptin Impurity D

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

  1. customTo a microwave vial equipped with a stir bar
  2. waitThe LCMS taken after 30 minutes

Sources & evidence

ORD record
ord-141a96a22f4c4386a39907b255737e90
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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