Compound 13
(3,5-dimethyl-4-(1-methyl-5-(pyridin-4-yl)-1H-imidazol-4-yl)phenyl)methanamine
From: Fragment-based discovery of a chemical probe for the PWWP1 domain of NSD3
View in PubChem | MDL Molfile | Chemdraw file
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
20 mg of 13 was synthesized analogously to 12 starting from 22. (Yields: 4% in the Suzuki step, 29% for the cyano reduction, quantitative for Boc removal): 1H NMR (500 MHz, DMSO-d6) δ 9.47 (br s, 1H), 8.73 (d, J=5.99 Hz, 2H), 8.52 (br s, 3H (protonated NH2)), 7.46 (d, J=5.99 Hz, 2H), 7.28 (s, 2H), 3.97 (q, J=5.70 Hz, 2H), 3.90 (s, 3H), 2.04 (s, 6H); 13C NMR (125 MHz, DMSO-d6) δ 148.8, 139.0, 136.5, 128.7, 128.6, 126.3, 124.8, 42.1, 35.3, 20.3, three carbons not visible; HRMS (m/z): [M+H]+ calculated for C18H21N4, 293.17607; found, 293.17505; HPLC-MS Rt = 0.80 min.
