Category: 75893-75-3

Reference of 75893-75-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 75893-75-3, name is 6-Cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below.

Example 56 6-Cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (56) In a 10-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, [2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methanamine (100 mg, 0.31 mmol, 1.00 equiv) and 6-cyclopropylpyridine-3-carboxylic acid (60.7 mg, 0.37 mmol, 1.20 equiv) were dissolved in N,N-dimethylformamide (2 mL), to which were added HATU (176.9 mg, 0.47 mmol, 1.50 equiv) and DIEA (120.3 mg, 0.93 mmol, 3.00 equiv) in sequence at room temperature. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by the addition of 5 mL water and the mixture was extracted with dichloromethane (3*10 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC using the following conditions: column, X Bridge C18, 19*150 mm, 5 um; mobile phase, acetonitrile in water (with 0.05% TFA), 30% to 70% gradient in 10 min; detector, UV, 254 nm. 6-cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (20 mg, 13%) was obtained as white solid. HPLC: 97.7% purity. MS: m/z=468.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 6 13.39 (br s, 1H), 9.20-9.17 (m, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.44 (s, 1H), 8.29-8.20 (m, 2H), 8.14-8.11 (m, 3H), 7.56-7.52 (m, 2H), 7.42 (d, J=8.0 Hz, 1H), 4.60 (s, 2H), 3.94 (s, 3H), 2.33-2.15 (m, 1H), 1.05-1.01 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75893-75-3, 6-Cyclopropylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75893-75-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 75893-75-3, name is 6-Cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below.

Example 56 6-Cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (56) In a 10-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, [2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methanamine (100 mg, 0.31 mmol, 1.00 equiv) and 6-cyclopropylpyridine-3-carboxylic acid (60.7 mg, 0.37 mmol, 1.20 equiv) were dissolved in N,N-dimethylformamide (2 mL), to which were added HATU (176.9 mg, 0.47 mmol, 1.50 equiv) and DIEA (120.3 mg, 0.93 mmol, 3.00 equiv) in sequence at room temperature. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by the addition of 5 mL water and the mixture was extracted with dichloromethane (3*10 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC using the following conditions: column, X Bridge C18, 19*150 mm, 5 um; mobile phase, acetonitrile in water (with 0.05% TFA), 30% to 70% gradient in 10 min; detector, UV, 254 nm. 6-cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (20 mg, 13%) was obtained as white solid. HPLC: 97.7% purity. MS: m/z=468.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 6 13.39 (br s, 1H), 9.20-9.17 (m, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.44 (s, 1H), 8.29-8.20 (m, 2H), 8.14-8.11 (m, 3H), 7.56-7.52 (m, 2H), 7.42 (d, J=8.0 Hz, 1H), 4.60 (s, 2H), 3.94 (s, 3H), 2.33-2.15 (m, 1H), 1.05-1.01 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75893-75-3, 6-Cyclopropylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75893-75-3, 6-Cyclopropylnicotinic acid, 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, 75893-75-3, blongs to pyridine-derivatives compound. Formula: C9H9NO2

Step-6: Synthesis of N-[3-bromo-2-[[tert-butyI(dimethyl)siIyl]oxymethyl]phenyl]-6- cyclopropyl-pyridine-3-carboxamide: To a solution of 6-cyclopropylpyridine-3-carboxylic acid (0.5 g, 3.06 mmol), 3-bromo-2-[[tert- butyl(dimethyl)silyl]oxymethyl]aniline (1.16 g, 3.67 mmol) and HOBt (0.495 g, 3.67 mmol) in DCM (15 mL) was added NMM (0.5 mL, 4-59 mmol) and EDCI.HCl (0.876 g, 4.59 mmol). The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction (as indicated by TLC), water (10 mL) was added to it and extraction was carried out using DCM (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified using column chromatography (Si02, 10% ethyl acetate in hexanes) to afford title compound (0.5 g, 35%). LCMS: m/z 461.2 (M + 1)+. NMR (400 MHz, CDC13) delta 0.15 (s, 6H), 0.87 (s, 9H), 1.05-1.10 (m, 2H), 1.1 1-1.51 (m, 2H), 2.06-2.16 (m, 1H), 5.1 1 (s, 2H), 7.19-7.23 (aromatics, 2H), 7.33 (d, J = 8.0 Hz, 1H), 8.03 (dd, J = 8.0, 2.0 Hz, 1H), 8.33 (d, J = 8.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, lH), 9.99 (s, lH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75893-75-3, its application will become more common.

Reference:
Patent; ADVINUS THERAPEUTICS LIMITED; THAKKAR, Mahesh; KOUL, Summon; BHUNIYA, Debnath; SINGH, Umesh; WO2013/157021; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 75893-75-3, name is 6-Cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Cyclopropylnicotinic acid

5-[(2R,3R)-3-amino-2-methylpiperidin-1-yl]-3-{[4-(oxan-4-yloxy)phenyl]amino}pyrazine-2- carbonitrile (102.8 mg, 0.25 mmol) was dissolved in DMF (4 mL), 6-cyclopropylnicotinic acid (62 mg, 0.38 mmol), DIPEA (0.2 mL, 1.26 mmol) and PyBOP (196 mg, 0.38 mmol) were added. The mixture was stirred at room temperature 1 h. Water and DCM were added and the mixture was extracted with DCM. The organic phase was dried over Na2SO4, filtered and evaporated to give a crude which was purified by silica flash chromatography with 50% to 100% ethyl acetate in cyclohexane to afford N-[(2R,3R)-1-(5-cyano-6-{[4-(oxan-4-yloxy)phenyl]amino}pyrazin-2- yl)-2-methylpiperidin-3-yl]-6-cyclopropylpyridine-3-carboxamide (120.7 mg, 87% yield) as a yellow solid. MS found for C31H35N7O3 as (M+H)+ 554.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 75893-75-3, 6-Cyclopropylnicotinic acid.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem