Hydrochloric Acid → HCID 59205149, compound

Participants

Reaction Steps

A solution of 2-amino-6-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide (54 mg, 0.2 mmol) and N3-benzyl-N1-(4-chloro-pyrimidin-2-yl)-N3,4-dimethyl-benzene-1,3-diamine (according to step a), 55 mg, 0.163 mmol) in 2-propanol (6 mL) and 1M HCl (0.32 mL) is heated under reflux for 1 h. Solvents are evaporated and the residue is adjusted to pH 8 by the addition of aqueous NH3. Partition between EtOAc and water, washing with 10% brine, drying of the organic phase (Na2SO4), evaporation of solvents, and chromatography (silica gel) of the residue gives 2-{2-[3-(benzyl-methyl-amino)-4-methyl-phenylamino]-pyrimidine-4-ylamino}-6-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide, eluted with EtOAc/hexanes 2:3. 1H-NMR (400 MHz, DMSO-d6): 2.20 (s, CH3C(4″)); 2.43 (s, NCH3); 3.90 (s, NCH2C6H5); 4.90 (q, J=9, OCH2CF3); 6.20 (d, J=5, H—C(5′)); 6.93 and 6.97 (2d, J=9; H—C(5), H—C(5″); 7.14-7.20, 7.20-7.34, and 7.34-7.4 (3m, NCH2C6H5, H—C(2″), H—C(6″), SO2NH2); 7.45 (t, J=8, H—C(4)); 8.05 (d, J=5, H—C(6′)); 8.12 (db, J=9, H—C(3′)); 9.12 (b, NH); 8.9-10.3 (NH).

Provenance & Evidence