Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24666-56-6,3-Aminopiperidine-2,6-dione hydrochloride,as a common compound, the synthetic route is as follows.,24666-56-6

3-nitrophthalic anhydride (I, 44.0 g, 0.23 mol), 3-amino-2,6-piperidinedione hydrochloride(II, 37.9 g, 0.23 mol) was dissolved in 600 mL of tetrahydrofuran (THF)Triethylamine (23.27 g, 0.23 mol) was then added dropwise to the system,The temperature of the control system was <20¡ãC . After the dropwise addition, the reaction was carried out for 30 min at room temperature, and the filter cake was filtered through THF (30 mL x 3) and dried in vacuo to give the intermediate 67.20 g in 91.0percent yield. As the paragraph descriping shows that 24666-56-6 is playing an increasingly important role. Reference£º
Patent; Shanghai Institute of Pharmaceutical Industry; China Institute of Pharmaceutical Industry; LI, JIAN QI; HUANG, DAO WEI; ZHOU, AI NAN; LIU, YU; ZHU, MIN YU; (9 pag.)CN103724323; (2016); B;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.160357-94-8,1-Acetyl-4-aminopiperidine,as a common compound, the synthetic route is as follows.

160357-94-8, A mixture of (S)-6-chloro-N-(2-hydroxy-3-(3-phenyl-6,7-dihydro- 1 Hpyrazolo [4,3-c]pyridin-5 (4H)-yl)propyl)pyrimidine-4-carboxamide (100 mg, 0.24 mmol), 1-(4-aminopiperidin-1-yl) ethanone (45 mg, 0.32 mmol), and triethylamine (0.1 mL) in 2-propanol (10 mL) was stirred at 80 C for 12 h. The solvent was evaporated and the resultingresidue was purified by preparative HPLC to give the TFA salt of the title compound (91 mg,73%) as white solid. ?H-NMR (400 MHz, CD3OD, ): 8.65 – 8.54 (m, 1 H), 7.59 – 7.54 (m,2 H), 7.53 -7.48 (m, 2 H), 7.46 – 7.40 (m, 1 H), 7.33 -7.09 (m, 1 H), 4.78 – 4.57 (m, 2 H),4.55 -4.46 (m, 1 H), 4.44- 4.24 (m, 2 H), 4.20 – 3.88 (m, 2 H), 3.86 – 3.46 (m, 5 H), 3.43 -3.35 (m, 1 H), 3.25 – 3.14 (m, 2 H), 2.96 -2.81 (m, 1 H), 2.18 -2.14 (m, 3 H), 2.05 (s, 2 H),1.63 – 1.44 (m, 2 H). LCMS (mlz): 519.2 (M+1).

As the paragraph descriping shows that 160357-94-8 is playing an increasingly important role.

Reference£º
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; SHAPIRO, Gideon; (393 pag.)WO2015/200677; (2015); A2;,
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333986-70-2, Methyl 4-(piperidin-4-ylmethyl)benzoate hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Example of General Method C: Preparation of 4-{l-[(S)-4-(2,3-Dihydro-benzo[l,4]dioxin-2-yl)-benzyl]-piperidin-4- ylmethylj-benzoic acid methyl ester A solution of A (100 mg, 0.42 mmol), 4-piperidin-4-ylmethyl-benzoic acid methyl ester hydrochloride (146 mg, 0.54 mmol), sodium cyanoborohydride (52 mg, 0.83 mmol), and TEA (0.08 mL, 0.54 mmol) in THF (5 mL) is treated with 2 drops of acetic acid, and stirred at room temperature for 16 h. The mixture is concentrated, and the residue is purified by flash chromatography eluting with a gradient of 0-10% MeOH in DCM to give the title compound.

333986-70-2, The synthetic route of 333986-70-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRUNETTE, Steven, Richard; ABEYWARDANE, Asitha; BURKE, Michael, J.; KAPADIA, Suresh, R.; KIRRANE, Thomas, Martin, Jr.; NETHERTON, Matthew, Russell; RAZAVI, Hossein; RODRIGUEZ, Sonia; SAHA, Anjan; SIBLEY, Robert; SMITH KEENAN, Lana, Louise; TAKAHASHI, Hidenori; TURNER, Michael, Robert; WU, Jiang-Ping; YOUNG, Erick, Richard, Roush; ZHANG, Qiang; ZHANG, Qing; ZINDELL, Renee, M.; WO2013/134226; (2013); A1;,
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1016258-66-4, 1-tert-Butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 26N-((lH-Indol-2-yl)methv?-4-(aminomethv?-l-(7H-pyrrolor2.3-d1pyrimidin-4- yl)piperidine-4-carboxamide26A. 1 -(tert-Butoxycarbonyl)-4-cvanopiperidine-4-carboxylic acid; A solution of lithium hydroxide (21.25 ml, 42.50 mmol) in water was added to a stirred solution of 1-tert-butyl 4-ethyl 4-cyanopiperidine-l,4-dicarboxylate (3g, 10.63 mmol), in THF (42.5 ml) at 250C. The resulting mixture was stirred at 25 0C for 18 hours. The reaction mixture was diluted with Et2O (100 mL), and washed with water (50 mL). The aqueous layers were combined and then acidified with citric acid (IN, 50 mL). The product was extracted into DCM. The organic layer was dried over MgSO4, filtered and evaporated to afford crude product l-(tert-butoxycarbonyl)-4-cyanopiperidine-4-carboxylic acid (2.73 g, 101 %) as a yellow liquid. IH NMR (400.13 MHz, DMSO-d6) delta 1.41 (9H, s), 1.78 – 1.85 (2H, m), 2.04 (2H, d) 2.95 (2H, t), 3.96 (2H, d), 13.9 (IH, s), 1016258-66-4

As the paragraph descriping shows that 1016258-66-4 is playing an increasingly important role.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75110; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.871022-62-7,tert-Butyl ((4-fluoropiperidin-4-yl)methyl)carbamate,as a common compound, the synthetic route is as follows.

[00344] Step a: A mixture of 3-((3-amino-2-chlorophenyl)thio)-6-chloropyrazin-2- amine (200 mg, 0.696 mmol) and tert-butyl ((4-fluoropiperidin-4-yl)methyl)carbamate (243 mg, 1.045 mmol), and DIPEA (0.6 mL, 3.48 mmol) in NMP (2 mL) was stirred for 16 h at 150 C. After cooling to RT, the reaction mixture was poured into a separation funnel containing brine and it was extracted with EtOAc (3 x 5 mL). The combined organic phases were dried over MgS04, filtered and the volatiles were removed under reduced pressure. The resulting residue was purified by silica chromatography (0 to 10% gradient of MeOH DCM) to give tert-butyl ((l-(6-amino-5- ((3-amino-2-chlorophenyl)thio)pyrazin-2-yl)-4-fluoropiperidin-4-yl)methyl)carbamate (285 mg, 0.590 mmol). MS m/z 483.1 (M+H)+.

871022-62-7, As the paragraph descriping shows that 871022-62-7 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KARKI, Rajesh; KATO, Mitsunori; LAMARCHE, Matthew J.; PEREZ, Lawrence Blas; WILLIAMS, Sarah; SENDZIK, Martin; WO2015/107494; (2015); A1;,
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4897-50-1, 4-Piperidinopiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

tert-Butyi 4-(6-ami -3-pyridyl)piperazine-l-carboxylate (0500) The compound was prepared as described in WO 2010/020675 Al . (0501) (0502) To 5-bromo-2-nitropyridine (1.2 g, 5.9 mmole) in DMSO (4 mL) was added l -(4- piperidyl)piperidine (1.0 g, 5.9 mmole) and triethylamine (0.99 mL, 7.1 mmole). The contents were heated to 120 C in a CEM Discovery microwave system for 3 hours. The crude reaction was then loaded over a silica gel column and eluted with DCM/methanol (0-20%) to afford 2- nitro-5-[4-(l-piperidyl)-l -piperidyl]pyridine as an oil (457 mg). NMR (600 MHz, DMSO-c e) delta ppm 1.26 – 1.36 (m, 2 H) 1.43 (m, 6 H) 1.76 (m, 2 H) 2.37 (m, 5 H) 2.94 (t, J=12.74 Hz, 2 H) 4.06 (d, J=13.47 Hz, 2 H) 7.41 (dd, J=9.37, 2.64 Hz, 1 H) 8.08 (d, J=9.37 Hz, 1 H) 8.20 (d, J=2.64 Hz, 1 H)

4897-50-1, The synthetic route of 4897-50-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copelnad; (156 pag.)WO2018/5863; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.79099-07-3,1-Boc-4-Piperidone,as a common compound, the synthetic route is as follows.,79099-07-3

[Reference Example 1] Synthesis of 6-aza-1-oxaspiro[2.5]octane-6-carboxylic acidtert-butyl ester After dissolving 60percent NaH-in-oil (5.28 g, 132 mmol) in DMSO (dimethylsulfoxide) (250 mL) cooled to 0¡ãC, trimethylsulfonium iodide (29.0 g, 132 mmol) was added. The reaction mixture was then raised to room temperature and the mixture was stirred for 40 minutes. N-Boc-piperidone (Boc = tert-butoxycarbonyl) (25.0 g, 125 mmol) was added to the reaction mixture, which was then stirred at room temperature for 1 hour and then at 55¡ãC for 1.5 hours. Next, the reaction mixture was poured into ice-cooled water (500 mL) and was extracted with AcOEt (ethyl acetate) (500 ml x 3 times). The organic layer obtained by combining the ethyl acetate layers was washed with water and then with saturated brine, and then dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated to obtain 6-aza-1-oxaspiro[2.5]octane-6-carboxylic acid tert-butyl ester. The compound was identified by 1H-NMR. The yield was 26.4 g (99percent). 1H-NMR (270 MHz, CDCl3): 1.40-1.49(m,2H), 1.46(s,9H), 1.74-1.85(m,2H), 2.69(s,2H), 3.37-3.48(m,2H), 3.68-3.77(m,2H).

As the paragraph descriping shows that 79099-07-3 is playing an increasingly important role.

Reference£º
Patent; TEIJIN LIMITED; EP1505067; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.71233-25-5,1-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate,as a common compound, the synthetic route is as follows.,71233-25-5

Intermediate 1, Step a: tert-Butyl 4-hydroxy-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate To a solution of 1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate (2.00 g, 7.39 mmol) in EtOH (37 mL) was added formamidine hydrochloride (910 mg, 11.08 mmol) followed by NaOEt (6.89 mL, 2.68 M in EtOH) dropwise. The mixture was then heated to reflux overnight. The mixture was concentrated in vacuo and then dissolved in a minimum amount of water. The pH was adjusted to pH 7 with 1 N HCl. The aqueous layer was then saturated with solid NaCl and extracted with a combination of EtOAc and DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography on SiO2 eluting with IPA/EtOAc afforded the desired product as a white solid (993 mg, 53percent). MS (ESI) mass calcd. C12H12N3O3, 251.13. m/z found 252.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.05 (s, 1H), 4.42 (s, 2H), 3.69-3.61 (m, 2H), 2.63 (s, 2H), 1.49 (s, 9H).

As the paragraph descriping shows that 71233-25-5 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; Alcazar Vaca, Manuel Jesus; Andres Gil, Jose Ignacio; Letavic, Michael A.; Rudolph, Dale A.; Shireman, Brock T.; Stenne, Brice M.; Ziff, Jeannie M.; US2014/275120; (2014); A1;,
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3970-68-1, 4-Methylpiperidin-4-ol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 13.1; 1-(4-{2-[6-(4-Methoxy-phenyl)-py?dazin-3-yloxy1-ethoxy)-benzyl)-4-methyl-piperidin-4-ol; 100 mg (0.285 mmol) 4-{2-[6-(4-Methoxy-phenyl)-pyridazin-3-yloxy]-ethoxy}-benzaldehyde (educt XII.1 ) and 35 mg (0.30 mmol) 4-methyl-pipeiotadin-4-ol are dissolved in 10 ml of THF and 0.20 ml cone, acetic acid are added. After 10 minutes 180 mg (0.855 mmol) sodium triacetoxyborohydride are added and the mixture is stirred for 20 hours at RT. After that time the mixture is filtered and the solvent is evaporated. The residue is purified by silica gel column chromatography with methylene chloride/methanol/ammonia (10:1 :0.1 ) as eluent. Yield: 50 mg (39% of theory),Rf value: 0.25 (silica gel, methylene chloride/methanol/ammonia = 10:1 :0.1 )EII mass spectrum: m/z = 450 [M+H]+

3970-68-1, The synthetic route of 3970-68-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/48802; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1454-53-1,Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

A suspension of ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (5a) (19.5 g, 68.7 mmol) and guanidine carbonate (19.5 g, 41.23 mmol) in ethanol (170 mL) was heated for 16 hours at 120C. The solvent was removed under reduced pressure, reconstituted in acetonitrile where the crude precipitated and was isolated by filtration. The solid was used as such in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) d ppm 2.35 – 2.46 (m, 2 H), 2.57 – 2.65 (m, 2 H), 3.04 (s, 2 H), 3.60 (s, 2 H), 6.28 (br. s., 2 H), 7.27 (dt, J=8.7, 4.5 Hz, 1 H), 7.31 – 7.36 (m, 4 H), 10.74 (br. s., 1 H). MS m/z: 257 [M+H]+.

1454-53-1, The synthetic route of 1454-53-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; McGowan, David C.; Herschke, Florence; Khamlichi, Mourad D.; Rosauro, Mari Luz; Benedicto, Sara M. Perez; Pauwels, Frederik; Stoops, Bart; Pande, Vineet; Scholliers, Annick; Van Schoubroeck, Bertrand; Mostmans, Wendy; Van Dijck, Kris; Thone, Tine; Horton, Helen; Fanning, Gregory; Jonckers, Tim H.M.; Raboisson, Pierre; Bioorganic and Medicinal Chemistry Letters; vol. 28; 19; (2018); p. 3216 – 3221;,
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