Diethanolamine → HCID 72202008, compound

Participants

Reaction Conditions

Reaction Steps

5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 44.2, 60 mg, 0.152 mmol), diethanolamine (19.14 mg, 0.182 mmol), DIPEA (53.0 μl, 0.303 mmol) and iPrOH (150 μl) were added to a vial, which was sealed and subjected to MW irradiation at 110° C. for 60 min, and then at 150° C. for 10 min. Diethanolamine (15.95 mg, 0.152 mmol) was then added and the RM was subjected to MW irradiation at 160° C. for 1 h. Pyrimidin-5-ylboronic acid (56.4 mg, 0.455 mmol), Pd(PPh3)2Cl2 (10.65 mg, 0.015 mmol) Na2CO3 (80 mg, 0.758 mmol) water (200 μL) and DME (600 μL)—were then added and the vial was resealed and stirred at 80° C. for 2.5 h. The RM was diluted with 1.5 mL of THF, stirred with Si-Thiol (Silicycle, 59.7 mg, 0.076 mmol) for 1 h, filtrated and the filtrate was evaporated to dryness under reduced pressure to give a residue which was purified by preparative HPLC (Condition 8, 20% for 0.2 min then 20% to 50% in 12 min) to yield the title compound as a white solid. UPLC-MS (Condition 1) tR=1.59 min, m/z=464.0 [M+H]+, m/z=462.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.83 (t, J=5.4 Hz, 2H) 3.18 (t, 2H) 3.53 (t, J=5.4 Hz, 2H) 4.61 (t, J=5.4 Hz, 2H) 4.90 (br. s, 1H) 7.40 (d, J=8.6 Hz, 2H) 7.88 (d, J=4.6 Hz, 2H) 8.52 (d, J=2.4 Hz, 1H) 8.84 (d, J=2.4 Hz, 1H) 9.20 (s, 2H) 9.23 (s, 1H) 10.49 (s, 1H).

Provenance & Evidence