Ammonium Chloride → HCID 53251706, compound

Participants

Reaction Steps

To a solution of 1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylic acid (15 mg, 0.033 mmol) in N,N-dimethylformamide (0.33 mL) was added ammonium chloride (5.4 mg, 0.10 mmol), diisopropylethylamine (23 μL, 0.13 mmol) and then (1H-benzotriazol-1-yloxy)(tripyrrolidin-1-yl)phosphonium hexafluorophosphate (35 mg, 0.067 mmol). After stirring for 90 minutes at room temperature, the mixture was diluted with EtOAc (30 mL), then washed with 1:1 saturated aqueous sodium bicarbonate:brine (2×30 mL). The aqueous fractions were further extracted with EtOAc (30 mL). The combined organic extracts were dried over sodium sulfate, and concentrated under reduced pressure. Purification by reverse phase HPLC provided 7 mg (0.016 mmol, 47% yield) of 1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]piperidine-4-carboxamide. MS APCI: [M+H]+ m/z 449.1. 1H NMR (400 MHz, DMSO): δ 10.26 (s, 1H); 8.84 (d, J=4.9 Hz, 1H); 8.01 (s, 1H); 7.57-7.49 (m, 2H); 7.35-7.26 (m, 3H); 7.16 (d, J=7.7 Hz, 1H); 6.85 (s, 1H); 3.93 (d, J=12.8 Hz, 2H); 3.14-2.98 (m, 2H); 2.42-2.31 (m, 1H); 1.91-1.69 (m, 2H); 1.69-1.55 (m, 2H). rhSyk=+++.

Provenance & Evidence