Application of 641571-11-1, A common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A solution of potassium t-butoxide (11 mL of 1M solution, 5.5 equiv.) in THF was slowly (10 min) added to compound 3b (0.77 g, 2.0 mmol) and 1-(3-amino-5-trifluoromethylphenyl)-4-methyl-1Himidazole (0.45 g, 2.0 mmol) dissolved in THF (30 mL) at -15 to -10 C under an argon atmosphere. The dark red solution was stirred at room temperature for 3.5 h and then cooled to 0 C and treated with saturated NaCl aqueous solution (25 mL). The organic layer was separated; the aqueous one was extracted with EtOAc (2×15 mL). Combined organic extracts were dried (Na2SO4) and evaporated. The yellow solid residue was treated with toluene (5-10 mL) and filtered off to obtain nilotinib trifluoromethyl derivative 7 (0.8 g, 67%) as yellow solid; m.p. 269-271 C (EtOH); 1H NMR: delta 2.14 (3H, s, CH3), 2.32 (3H, s, CH3), 7.44 (1H, s, 5-H imidazole), 7.46 (1H, d, J = 8.1 Hz, 5-H), 7.50 (1H, dd, J = 8.0, 4.8 Hz, 5-H Py), 7.69 (1H, s, 2-H imidazole), 7.79 (1H, dd, J = 8.1, 1.7 Hz, 6-H), 7.88 (1H, s, Pm), 8.11 (1H, s, 2-H Ar), 8.16 (1H, d, J= 1.7 Hz, 2-H), 8.20 (1H, s) and 8.25 (1H, s) 4,6-H Ar, 8.48 (1H, dt, J= 8.0, 1.7 Hz, 4-H Py), 8.68 (1H, dd, J= 4.8, 1.7 Hz, 6-H Py), 9.29 (1H, d, J= 1.7 Hz, 2-H Py), 9.83 (1H, s, NH), 10.57 (1H, s, NH). 13C NMR: delta 13.5 (CH3), 18.2 (CH3), 103.2 (q, J= 3 Hz, C-5 Pm), 111.6 (q, J= 4 Hz, C-6 Ar), 114.2, 114.3 (q, J= 4 Hz, C-4 Ar), 115.0 (C-2 Ar), 120.7 (q, J= 274 Hz, CF3), 123.6 (q, J= 271 Hz, CF3), 123.8 (C-5 Py), 124.5, 124.8, 130.7, 130.8 (q, J= 32 Hz, C-CF3), 131.2, 131.9, 134.8 and 134.9 (C-4 Py, C-3), 137.3, 137.7, 137.9, 138.9, 141.3, 148.5 (C-6 Py), 152.2 (C-2 Py), 156.5 (q, J= 35 Hz, C-CF3Pm), 161.1 (C-4 Pm), 165.1 (C=O), 165.4 (C-2 Pm). Anal. calcd for C29H21N7F6O: C, 58.29; H, 3.54; N, 16.41; found: C, 58.30; H, 3.65; N, 16.22%.
The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Terentjeva; Muceniece; Lusis; Journal of Chemical Research; vol. 39; 4; (2015); p. 223 – 225;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem