benzo[d]oxazole-6-carboxylic acid

N-(5-((5-(4-(dimethylcarbamoyl)phenyl)pyridin-2-yl)amino)pyridin-3- yl)benzo [d] oxazole-6-carboxamide. [0703] To a mixture of 4-(6-((5-aminopyridin-3-yl)amino)pyridin-3-yl)-N, N- dimethylbenzamide (50 mg, 0.15 mmol) in pyridine (2 mL) was added benzo[d]oxazole-6- carboxybc acid (37 mg, 0.22 mmol) and EDOHC1 (43 mg, 0.22 mmol), the reaction mixture was stirred at 50 C for 2 h to give a brown suspension. LCMS (Rt = 1.152 min; MS Calc'd: 478.2; MS Found: 479.2 [M+H]+). The mixture was concentrated under reduced pressure to give a residue. The residue was purified by washing with MeOH/water (5 mL/l mL) to give a crude product. The impure product was further purified by prep-HPLC (0.05% NH3.H2O as an additive) to give an impure product. Then further purified by washing with MeOH (2 mL) to give N-(5-((5-(4-(dimethylcarbamoyl)phenyl)pyridin-2-yl)amino)pyri din-3- yl)benzo[d]oxazole-6-carboxamide (5.2 mg, yield: 7%) as a white solid. LCMS (Agilent LCMS 1200-6140 A, mobile phase: from 99% [water + 0.1% FA] and 1% [MeCN + 0.1% FA] to 95% [water + 0.1% FA] and 5% [MeCN + 0.1% FA] in 0.6 min, then changed to 100% [MeCN + 0.1% FA] under this condition for 3.4 min, finally back to 99% [water + 0.1% FA] and 1% [MeCN + 0.1% FA] and under this condition for 0.5 min.) purity is 98.01%, Rt = 2.231 min; MS Calc'd.: 478.2; MS Found: 479.3 [M+H]+. NMR (400 MHz, DMSO-rfc) d 2.94- 3.06 (6H, m), 7.01 (1H, d, J= 8.4 Hz), 7.49 (2H, d, J= 8.4 Hz), 7.73 (2H, d, J= 8.4 Hz), 7.97 (1H, d, J= 8.4 Hz), 8.01 (1H, dd, J= 8.4, 2.4 Hz), 8.07 (1H, dd, J= 8.0, 2.0 Hz), 8.44 (1H, d, J= 1.2 Hz), 8.53 (1H, d, J= 2.0 Hz), 8.59 (1H, d, J= 2.4 Hz), 8.70-8.75 (2H, m), 8.95 (1H, s), 9.53 (1H, br s), 10.55 (1H, br s), A mixture of l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4, 3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), A mixture of l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4, 3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.General procedure: A solution containing 4-methoxybenzoic acid (0.46 g, 3.0 mmol), HOBTH2O (0.46 g, 3.0 mmol) and dry DMF (20 mL) wascooled to 0 C. EDCI (0.86 g, 4.5 mmol) was added to the solution.The mixture was stirred at room temperature for 30 min thencooled to 0 C. Compound 6 (0.70 g, 2.0 mmol) was added to themixture and stirred for 48 h at room temperature. The reactionmixture was poured into ice-water (100 mL). The resulting precipitatewas collected by filtration and purified by recrystallizationfrom DMF/EtOAc. Yellow solid (0.60 g, 62%), m.p. 286e288 C.

Molecular Weight:163.13
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:163.026943022
Monoisotopic Mass:163.026943022
Topological Polar Surface Area:63.3
Heavy Atom Count:12
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes