Potassium Carbonate → HCID 54671131, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-Chloroethyl)morpholine hydrochloride (31.93 mg, 0.1716 mmol) was added to a stirred solution of 3-[2-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]ethynyl]phenol (45 mg, 0.1144 mmol) and K2CO3 (39.53 mg, 0.2860 mmol) in DMF (1 mL) and the reaction mixture warmed to 65° C. for 16 hours. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3 and stirred for 5 minutes. The layers were separated by filtration through a phase separation cartridge and the aqueous layer retained was washed with DCM (×2). The combined organic extracts were passed through a 5 g SCX-2 cartridge and washed with MeOH. The product was eluted by washing the cartridge with 2M NH3 in MeOH. The solvent was removed in vacuo and the material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the mono-TFA salt of the title compound as a yellow solid (29 mg, 41% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.09 (d, 6H), 3.22-3.25 (m, 2H), 3.41-3.74 (m, 7H), 4.01 (d, 2H), 4.43 (s, 2H), 6.98 (s, 2H), 7.14 (d, 1H), 7.41-7.48 (m, 3H), 7.92 (d, 2H), 8.23 (d, 2H), 8.78 (s, 1H) and 9.88 (s, 1H) ppm; (ES+) 507.3.

Provenance & Evidence