4-(2-Pyridyl)benzoicacid

This synthetic procedure was adapted from Ref. [58]. Tolylpyridine was oxidized with KMnO4 as follows: a mixture of tolylpyridine(0.514 g) and KMnO4 (1.54 g) inwater 50 mL was heated at70 °C for 24 h. After filtration of the reaction mixture and washing the filtrate with aqueous NaOH (1M, 5 mL), the combined water fraction were collected and washed three times with CHCl3 to remove unconverted starting material. The aqueous solution wasneutralized with HCl (1M) and concentrated (30 mL). After acidifyingto pH 4, the precipitate was collected, washed with ethanoland dried in vacuum yielding a white powder. (Yield 85percent) 1H NMR(400 MHz, CD3OD) δ:8.57 (d, 3J = 4.46, 1H, Py-H); 8.05 (d, 3J = 8.23, 2H, Ar-H); 7.97 (d, 3J = 8.23, 2H, Ar-H); 7.87 (d, 3J = 3.43, 1H, Py-H);7.37-7.33 (m, 2H, Py-H). 13C {1H} NMR (400 MHz, DMSO-d6): 168.04, 154.59, 148.75, 141.78, 139.90, 131.51, 130.44, 129.98, 127.55, 124.50, 122.69. HRMS (ESI) m/z calcd 199.0633 for C12H9NO2, found200.0706 (M+H)+Example 155 A4-(pyridin-2-yl)benzoic acid; To a solution of 4-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) were added. The mixture was degassed and purged withed nitrogen. The mixture was stirred under reflux for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=4 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.81 g of white solid of 4-(pyridin-2-yl)benzoic acid. Yield: 91percent. LC-MS (ESI) m/z: 200 (M+1)4-pyridin-2-ylbenzoic acid Example 107 10-(4-PYRIDIN-2-YLBENZOYL)-N-(PYRIDIN-3-YLMETHYL)-10, 11-DIHYDRO-5H-PYRROLO[2, 1-C][1, 4]BENZODIAZEPINE-3-CARBOXAMIDE Step A. 4-Pyridin-2-ylbenzoic acid; To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 2-bromopyridine (0.38 mL, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added and the reaction mixture heated to 90° C. for 20 hours. The hot mixture was filtered through celite and concentrated in vacuo to remove acetonitrile. The resulting aqueous suspension was diluted with water (20 mL), washed with dichloromethane (2.x.40 mL), and then acidified to pH 6 by the addition of concentrated hydrochloric acid. The resulting white suspension was diluted with water (20 mL), filtered and the solid product dried in vacuo at 50° C. overnight to give the title compound (0.662 g, 84percent) as a white solid, m.p. 232-234° C. MS [(+)ESI, m/z]: 200 [M+H]5.1.4

Reactive metabolite of Atazanavir (A790051).

Molecular Weight:199.20
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:199.063328530
Monoisotopic Mass:199.063328530
Topological Polar Surface Area:50.2
Heavy Atom Count:15
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes