O-Phenylenediamine → HCID 44612007, compound

Participants

Reaction Steps

To the above ester in EtOH/THF (10:3) (13 mL) was added 3N NaOH (4.5 mL) and stirred at room temperature. After 14 hours, the reaction mixture was concentrated, diluted with water and washed with ether (30 mL). The aqueous phase was then neutralized with 6N HCl (1.5 mL) and then extracted with ethyl acetate and dried (MgSO4). The mixture was then filtered, concentrated and diluted with water and acetonitrile and directly purified by preparative HPLC giving 4-[4-(3-isopropyl-2-methyl-3H-imidazol-4-yl)-[1,3,5]triazin-2-ylamino]-benzoic acid. MS found for C17H18N6O2 as (M+H)+ 339.06. To the above carboxylic acid (150 mg, 0.4 mmol) in NMP (3 mL), was added HATU (228 mg, 0.60 mmol), 1,2-phenylenediamine (95 mg, 0.90 mmol) and NMM (0.2 mL, 1.60 mmol) and stirred for 16 hours. The reaction mixture was diluted with water and acetonitrile and directly purified by preparative HPLC affording the title compound, after lyophilization. MS found for C23H24N8O as (M+H)+ 429.09. 1H NMR (400 MHz, dmso-d6): δ 9.85 (s, 1H); 9.21 (s, 1H); 8.85 (s, 1H); 8.30 (s, 1H); 7.99 (d, J=8.4 Hz, 2H); 7.79 (m, 2H); 7.21 (d, J=7.6 Hz, 1H); 7.08-6.84 (m, 3H); 5.89 (septet, J=6.8 Hz, 1H); 2.71 (s, 3H); 1.53 (d, J=6.8 Hz, 6H).

Provenance & Evidence