Trifluoroacetic acid → HCID 68379418, compound

Participants

Reaction Steps

To a stirred solution of (S)-tert-butyl 4-(3-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzylamino)piperidine-1-carboxylate (110 mg, 0.184 mmol) in 2 mL of DCM was added 2 mL of 2,2,2-trifluoroacetic acid. The solution was stirred at room temperature overnight. The mixture was washed with NaHCO3(aq.), the organic layer was concentrated. The residue was purified by preparative HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 ml/inj, flow rate: 20 ml/min; wavelength: 214 nm and 254 nm; the gradient conditions are: 40% acetonitrile/60% water (0.1% TFA V/V) initially, and then proceed to 55% acetonitrile/45% water (0.1% TFA V/V) in a linear fashion after just 9 min.) to give (S)—N-(3-(2-methylpyrrolidin-1-yl)phenyl)-5-(3-((piperidin-4-ylamino)methyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine 2,2,2-trifluoroacetate (40 mg, 43%) as an oil. 1H NMR (300 MHz, DMSO): δ 9.18 (s, 1H), 8.60 (s, 1H), 8.51 (dd, 1H, J1=7.5 Hz, J2=1.2 Hz), 7.92 (s, 1H), 7.84 (brs, 1H), 7.68-7.52 (m, 3H), 7.15 (brs, 1H), 4.40 (s, 2H), 4.08-4.01 (m, 2H), 3.87-3.85 (m, 1H), 3.64-3.55 (m, 4H), 3.17-3.08 (m, 2H), 2.48-2.21 (m, 5H), 2.03-1.87 (m, 3 h), 1.34 (d, 3H, J=6.3 Hz). LC-MS: 250 [M/2+H]+, 500 [M+H]+, tR=1.20 min. HPLC: 100% at 214 nm, 100% at 254 nm, tR=4.59 min.

Provenance & Evidence