Category: 6320-39-4

Adding a certain compound to certain chemical reactions, such as: 6320-39-4, 3-Amino-4-hydroxypyridine, 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, Quality Control of 3-Amino-4-hydroxypyridine, blongs to pyridine-derivatives compound. Quality Control of 3-Amino-4-hydroxypyridine

To a large screw cap vial was added 3-aminopyridin-4-ol (0.440 g, 4.0 mmol) in DMF (lOmL) along with triethylamine (1.561 mL, 1 1.2 mmol), -(tert- butoxycarbonylamino)cyclopropanecarboxylic acid (0.845 g, 4.2 mmol) and finally TBTU, o-Benzotriazol-l-yl-N,N,N’,N’-tetramethyluronium tetrafluoroborate (1.605 g, 5.0 mmol). The vial was sealed and the brown mixture was shaken for 24 hours at room temperature. The reaction mixture was concentrated to an oil, taken up in acetonitrile and purified using a Shimadzu preparative HPLC employingacetonitrile/water/ammonium acetate where solvent A was 5% acetonitrile / 95% water / 10 mM ammonium acetate and solvent B was 5% water / 95% acetonitrile / 10 mM ammonium acetate with a Phenomenex-Luna IotaOmicronmuiotaeta C18 30x100mm column at a gradient of 0-100% B and a flow rate of 30mL/min. over 10 minutes with a 5 minute hold. Solvent was removed giving l.Ogram (81% yield) of tert-butyl l-(4- hydroxypyridin-3-ylcarbamoyl) cyclopropyl carbamate as a light yellow solid. The LC/MS data was obtained on a Shimadzu analytical LC /Micromass Platform LC (ESI+) at 220nm using the following set of conditions: Phenomenex Luna 3muetaiota CI 8, 2 x 50mm column, with a gradient of 0-100%B (B = 90% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 10% HPLC grade water), (A = 90% HPLC grade water / 0.1% trifluoroacetic acid/ 10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute. HPLC purity was determined using a Shimadzu analytical LC at 254nm and 256nm with a Waters Sunfire CI 8 3.5muiotaeta 4.6 x 150mm column employing water/acetonitrile/ 0.1% trifluoroacetic acid with a gradient of 10-100% B (B = 95% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 5% HPLC grade water), (A = 95% HPLC grade water / 0.1% trifluoroacetic acid/ 5% HPLC grade acetonitrile), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. The HPLC purity was then confirmed with an orthogonal solvent system and column using a Shimadzu analytical LC with a Phenomenex Gemini CI 8 3.0muiotaeta 4.6 x 150mm column employing water/methanol/ lOmM ammonium bicarbonate with a gradient of 10-100%) B (B = 95% HPLC grade methanol/ lOmM ammonium bicarbonate / 5% HPLC grade water), (A = 95% HPLC grade water / lOmM ammonium bicarbonate / 5% HPLC grade methanol), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. XH NMR (400 MHz, CD3OD) delta ppm 1.17 (m, 2 H), 1.51 (s, 9 H), 1.59 (m, 2 H), 6.55 (d, J=7.03 Hz, 1 H), 7.74 (dd, J=7.03, 1.51 Hz, 1 H), 7.79 (br. s., 1 H), 8.89 (d, 1 H). LCMS rt =1.682, min., m/z 294.3(M + H). HPLC rt = 5.621min. (Sunfire C18), 94.9% purity and 7.961min. (Gemini C18), 100 % purity

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6320-39-4, 3-Amino-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; GRANT-YOUNG, Katharine, A.; KADOW, John, F.; WO2011/112769; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6320-39-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 6320-39-4, name is 3-Amino-4-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 113-(1-[1,3]oxazolo[4,5-c]pyridin-2-ylpyrrolidin-3-yl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (One Enantiomer Isolated) A solution of 3-aminopyridin-4-ol (0.250 g, 2.27 mmol, Bosche Scientific) and potassium O-ethyl dithiocarbonate (0.400 g, 2.50 mmol) in ethanol (1 mL) was heated to reflux. When the reaction was determined complete, it was cooled to ambient temperature and partitioned between 1N HCl and ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, decanted and concentrated. This crude product was dissolved in toluene (6 mL) and thionyl chloride (0.365 mL, 5.01 mmol) followed by DMF (3 microL) was added. The mixture was heated to reflux for 1 h, cooled and the solvent removed in vacuo. A portion of this crude product (14 mg) was dissolved in 1,4-dioxane (0.40 mL), along with 3-pyrrolidin-3-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (20.0 mg, 0.0457 mmol, enantiomer 2 from Example 9, Step 2b), and N,N-diisopropylethylamine (16 microL, 0.091 mmol) was added. The mixture was heated to 70 C. for 1.5 h. The solvent was removed in vacuo and the residue was sequentially stirred with 50% TFA/DCM for 1.5 h, concentrated, and stirred with 0.3 mL EDA in methanol for 30 min. Purification via preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) afforded product. 1H NMR (400 MHz, d6-DMSO): delta 8.89 (s, 1H), 8.68 (s, 1H), 8.44 (s, 1H), 8.11 (dd, 1H), 7.72 (dd, 1H), 7.60 (d, 1H), 6.99 (d, 1H), 6.96 (dd, 1H), 4.88 (dt, 1H), 3.90 (dd, 1H), 3.71-3.63 (m, 1H), 3.58-3.30 (m, 4H), 3.04-2.93 (m, 1H), 1.80-1.66 (m, 2H); LCMS (M+H)+: 426.1.

According to the analysis of related databases, 6320-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6320-39-4 , The common heterocyclic compound, 6320-39-4, name is 3-Amino-4-hydroxypyridine, molecular formula is C5H6N2O, 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.

Step 1 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) piperidin-3-amine (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimeth yl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (100 mg, 0.24 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by the addition of 3-amino-4-hydroxypyridine (32.12 mg, 0.29 mmol) and potassium carbonate (67.19 mg, 0.49 mmol), then stirred at 60 C. overnight. After the reaction was completed, the reaction solution was diluted with water and then extracted with dichloromethane. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and separated by a preparative plate (Develop: EtOAc_MeOH=10:1) to give 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) piperidin-3-amine 339 (30 mg, yield: 28.01%). MS m/z (ESI): 441.2 [M+1] 1H NMR (400 MHz, CDCl3) 8.16 (s, 1H), 8.00 (s, 1H), 6.76 (s, 1H), 4.91 (s, 1H), 4.61-4.59 (m, 2H), 4.18 (s, 1H), 4.04-4.01 (m, 2H), 3.55-3.48 (m, 2H), 2.44 (d, J=12.0 Hz, 1H), 2.33-2.23 (m, 1H), 2.08-1.43 (m, 16H), 1.37 (s, 3H), 1.25-1.15 (m, 3H), 0.79 (s, 3H).

The synthetic route of 6320-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem