Adding a certain compound to certain chemical reactions, such as: 33420-52-9, 2,2-Difluoropropan-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 33420-52-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 33420-52-9
To a cooled (0 C) solution of 2,2-difluoropropan-1-ol (193 mg, 2.010 mmol) and pyridine (0.163 mL, 2.010 mmol) in CH3CN (20 mL) was added dropwise Tf2O (0.312 mL, 1.849 mmol). The reaction was maintained at 0 C for 30 min. To a suspension of 5-((2-(benzyloxy)-4,6-dimethylpyridin-3-yl)methyl)-3-methyl- 2-(1-(piperidin-4-yl)propyl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one (208 mg, 0.402 mmol) and K2CO3 (500 mg, 3.62 mmol) in CH3CN (20 mL) was added the above cold reaction mixture (containing 2,2-difluoropropyl trifluoromethanesulfonate). The reaction was allowed to warm to RT, then heated to 50 C overnight. The reaction was filtered and evaporated to dryness under vacuum. The residue was dissolved in EtOAc and the resultant solution was washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum to give an oil. A solution of the above oil in TFA (5 mL, 64.9 mmol) was maintained for 30 min, at which time it was concentrated. The reaction mixture was purified by preparative HPLC (5 to 60% MeCN: water with 0.1 % formic acid). The product containing fractions were treated with 6 M HC1 (0.5 mL) and concentrated to give 2-(1-(1-(2,2- difluoropropyl)piperidin-4-yl)propyl)-5-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3- yl)methyl)-3-methyl-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one (90 mg, 0.169 mmol, 42.1% yield) as white solid. 1H NMR (400 MHz, MeOH-d4) delta 7.07 (s, 1H), 4.82 (s, 2H), 3.88-3.99 (m, 2H), 3.72-3.86 (m, 3H), 3.65 (d, J=12.63 Hz, IH), 3.07-3.27 (m, 4H), 2.80- 2.91 (m, IH), 2.69 (s, 3H), 2.54 (s, 3H), 2.40 (s, 2H), 2.27 (d, J=14.15 Hz, IH), 2.00 (ddd, J=3.79, 7.20, 13.52 Hz, IH), 1.57-1.89 (m, 7H), 1.47 (ddd, J=7.07, 11.18, 13.58 Hz, IH), 0.80 (t, J=7.33 Hz, 3H). MS(ES) [M+H]+ 506.3.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (112 pag.)WO2016/66697; (2016); A1;,
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