Reference of 1019021-85-2 ,Some common heterocyclic compound, 1019021-85-2, molecular formula is C8H5FN2O2, 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.
To a solution of 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (13a) (210 mg, 1 .2 mmol) in dichloromethane (8 mL) was added oxalyl chloride (250 muIota, 2.8 mmol) and DMF ( 40 muIota) at 0-10 C. The resulting solution was stirred 30 min at room temperature and concentrated under vacuum. A solution of 3-amino-4-fluoro-N-((1 R,2S)-2-hydroxy-2,3- dihydro-1 H-inden-1 -yl)benzamide (16) (350 mg, 1 .2 mmol) in 3 mL of pyridine was added into the above obtained solid. The resulting solution was stirred 30 minutes at room temperature The above solution was purified by preparative mass trigger LCMS to afford N-(2-fluoro-5-(((1 R,2S)-2-hydroxy-2,3-dihydro-1 H-inden-1 -yl)carbamoyl) phenyl)- 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (F27) as a light yellow solid. 1 H NMR (400MHz, d6-MeOH) delta 9.57 (dd, J = 4.8, 2.4 Hz 1 H), 8.60 (s, 1 H), 8.35 (dd, J = 7.2, 2.4 Hz, 1 H), 7.80-7.85 (m, 2H), 7.65-7.71 (m, 1 H) 7.18-7.37 (m, 5H), 5.54 (d, J = 5.2 Hz, 1 H), 4.65 (td, J = 8.4, 2.0 Hz, 1 H), 3.18 (dd, J = 16, 5.2 Hz,1 H), 2.97(dd, J = 16.4, 2.0 Hz, 1 H). (MS m/z 449.1 (M+1 )+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1019021-85-2, its application will become more common.
Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
Pyridine – Wikipedia,
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