Trifluoroacetic acid → HCID 66780118, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl {[4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]thio}acetate (182 mg, 0.348 mmol) in Dichloromethane (DCM) (2 mL) in a 20 mL Scintillation vial stirred at rt was added TFA (2 mL, 26.0 mmol). After sitting at rt for 5 hr LC/MS analysis indicated complete conversion to the acid. The DCM/TFA was removed in vacuo and the resulting residue was taken up in DCM. Attempts to extract the desired product into 1 N NaOH solution led to emulsions, so the pH was adjusted to 2 and the DCM layer was concentrated and to the residue was added water and the resultant solid was isolated by filtration and then purified by reverse phase prep HPLC on 30 mm prep column eluting with a gradient 25% to 55% AcCN over 12 minutes. LC/MS (ES) m/z=467 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 7.35 (d, 1H), 7.09 (t, 1H), 6.61 (d, 1H), 5.56 (s, 2H), 4.01 (s, 2H), 3.83 (m, 4H), 3.59 (m, 4H), 2.49 (s, 3H).

Provenance & Evidence