Downstream synthetic route of 336191-17-4

336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.336191-17-4,tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate,as a common compound, the synthetic route is as follows.

The compound of formula 1-2 (methyl4-((4-bromo- 1 H-pyrrolo[2,3-b]pyridin- 1 -yi)methyl)benzoate) (0.700 g, 2.028 mmol), tert-butyl 2,8-diazabicyclo[4.5]decane-2-carboxylate (0.585 g, 2.433 mmol), Pd(t-Bu3P)2C12 (0.104 g, 0.203 mmol) and sodium tert-butoxide (0.234 g, 2.433 mmol) were dissolved in toluene (4 mL) at room temperature, and the solution was stirred at 120C for 17 hours, and then cooled to room temperature. After completion of the reaction, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified by column chromatography (Si02, 12 g cartridge; ethyl acetate/hexane = from 0% to 30%) to afford the desired compound of formula 18-1 (0.464 g, 45.3%) as a colorless oil., 336191-17-4

336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Changsik; YANG, Hyun-mo; LEE, Changkon; BAE, Miseon; KIM, Soyoung; CHOI, Youngil; HA, Nina; LEE, Jaekwang; OH, Jungtaek; SONG, Hyeseung; KIM, Ilhyang; CHOI, Daekyu; MIN, Jaeki; LIM, Hyojin; BAE, Daekwon; WO2015/87151; (2015); A1;,
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New learning discoveries about 336191-17-4

336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

336191-17-4, tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,336191-17-4

Step A: teri-Butyl 8-(2-chlorofuro[3,2-i/]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2- carboxylateA mixture of teri-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (0.83 g, 3.4 mmol, Alfa Aesar), 2,4-dichlorofuro[3,2-i/]pyrimidine (0.65 g, 3.4 mmol, ArkPharm) and TEA (0.96 mL, 6.9 mmol) in 1,4-dioxane (35 mL) was stirred at about 25 C for about 12 h. Water (4 mL) and EtOAc (25 mL) were added and the layers were separated. The organic layer was concentrated under reduced pressure to give teri-butyl 8-(2-chlorofuro[3,2-i/]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2- carboxylate (1.25 g, 55%): LC/MS (Table 2, Method f) Rt = 2.12 min; MS m/z: 393 (M+H)+.

336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
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New learning discoveries about 336191-17-4

336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

336191-17-4, tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

336191-17-4, EXAMPLE 16; 8-(5-{[(4-Aminobiphenyl-3-yl)amino]carbonyl}pyridin-2-yl)-N-(2-phenylethyl)-2,8-diazaspiro[4.5]decane-2-carboxamide; To a solution of methyl 6-chloronicontinate (200 mg, 1.16 mmol) in DMSO/PhMe (2 mL of a 1:1 solution) was added t-butyl-2,8-diazaspiro[4.5]decane-2-carboxylate (700 mg, 2.91 mmol). The reaction mixture was heated at 85 C. for 6 hours and then diluted with EtOAc (10 mL). The organic layer was washed with NaHCO3 (1¡Á5 mL) and brine (1¡Á5 mL), dried over Na2SO4, and then concentrated. The crude residue was purified by reverse-phase flash chromatography (10-100% MeCN/H2O with 0.05% TFA) to give t-butyl 8-[5-(methoxycarbonyl)pyridin-2-yl]-2,8-diazaspiro[4.5]decane-2-carboxylate: MS (ESI+): cal’d [M+H]+ 376.2, obs’d 376.2.

336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
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Analyzing the synthesis route of 336191-17-4

336191-17-4, As the paragraph descriping shows that 336191-17-4 is playing an increasingly important role.

336191-17-4, tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of compound 24 (300.00 mg, 1.25 mmol, 1.00 eq.) and benzoic acid (183.18 mg, 1.50 mmol, 1.20 eq.) in DCM (6 mL) was added NMM (252.88 mg, 2.50 mmol, 2.00 eq.) and T3P (1.19 g, 1.88 mmol, 1.50 eq.). The mixture was stirred at 25 C for 4 hrs.Then the mixture was purified by TLC (PE:EtOAc=1:1) to compound 25 (310.00 mg, 899.99 umol, 72.00% yield). To a solution of compound 25 (310.00 mg, 899.99 umol, 1.00 eq.) in DCM (2 mL) was added HCl/AcOEt (30mL) at 0 C. The mixture was stirred at 25 C for 2 hrs. Then it was concentrated to dryness to give compound 26 (300.00 mg, crude). To a solution of compound 6 (20.00 mg, 66.39 umol, 1.00 eq.) and compound 26 (19.47 mg, 79.67 umol, 1.20 eq.) in pyridine (3.00 mL) was added EDCI (19.09 mg, 99.59 umol, 1.50 eq.) at 25 C , the mixture was stirred for 3 h our at 25 C. LCMS showed the SM consumed, desired product was formed as major product. The reaction was concentrated, dissolved in to DMF (3 mL), purified by prep-HPLC (base condition) and concentrated to give SC27 (11.00 mg, 20.37 umol,30.68% yield, 97.7% purity) as yellow gum.

336191-17-4, As the paragraph descriping shows that 336191-17-4 is playing an increasingly important role.

Reference£º
Article; Tuyishime, Marina; Lawrence, Rae; Cocklin, Simon; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 228 – 234;,
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Downstream synthetic route of 336191-17-4

336191-17-4, 336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.336191-17-4,tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate,as a common compound, the synthetic route is as follows.

tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (7.21 g, 30.0 mmol) is dissolved in TEA (7.69 mL) in DCM (200 mL) at 0 C. and treated dropwise with cyclobutanone (2.92 mL, 38.9 mmol). The mixture is stirred for 30 min and sodium triacetoxyborohydride (9.53 g, 4.56 mmol) is added in portions. The reaction mixture is stirred at rt overnight, basified with 1N NaOH solution and extracted with DCM (2¡Á100 mL). The combined extracts are washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford the title compound. LC-MS (Method 1): 295.4.

336191-17-4, 336191-17-4 tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate 34178604, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Xu, Yuelian; Caldwell, Timothy M.; Xie, Linghong; Chenard, Bertrand L.; US2008/247964; (2008); A1;,
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Downstream synthetic route of 336191-17-4

As the paragraph descriping shows that 336191-17-4 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.336191-17-4,tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate,as a common compound, the synthetic route is as follows.

[00139] Step 1) A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (Intermediate 10, 1.00 g, 4.16 mmol), 4-fluoropyridine hydrochloride (Intermediate 15, 614 mg, 4.60 mmol) and K2CO3 (1.74 g, 12.6 mmol) in MeCN (80 mL) was heated at 80C overnight before cooling to rt and concentration in vacuo. The residue was partitioned between EtOAc and H2O, the organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo. (0324) Purification by gradient flash chromatography, eluting with 0-100% solvent B in DCM (where solvent B is 7N NH3 in MeOH / DCM, 1:9) yielded tert-butyl 8-(pyridin-4-yl)-2,8- diazaspiro[4.5]decane-2-carboxylate (610 mg, 1.92 mmol) as a brown, viscous oil. (0325) LCMS (Method B): m/z 318.2 (ES+), at 1.36 min. (0326) 1H NMR: (400 MHz, CD3OD) delta: 1.46 (s, 9H), 1.63-1.68 (m, 4H), 1.81-1.85 (m, 2H), 3.23 (s 2H), 3.36-3.54 (m, 6H), 6.82-6.83 (m, 2H), 8.07-8.09 (m, 2H)., 336191-17-4

As the paragraph descriping shows that 336191-17-4 is playing an increasingly important role.

Reference£º
Patent; HEPTARES THERAPEUTICS LIMITED; BUCKNELL, Sarah Joanne; CHRISTOPHER, John Andrew; CONGREVE, Miles Stuart; DEFLORIAN, Francesca; PICKWORTH, Mark; MASON, Jonathan Stephen; (201 pag.)WO2018/178938; (2018); A1;,
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Simple exploration of 336191-17-4

The synthetic route of 336191-17-4 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.336191-17-4,tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate,as a common compound, the synthetic route is as follows.

Step-1: tert-Butyl 8-(5-(trifluoromethyl)pyrimidin-2-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate Sodium t-butoxide (625 mg, 6.51 mmol, 3.0 eq.) was added to a stirred solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (600 mg, 2.17 mmol, 1.0 eq.) and 2-chloro-5-(trifluoromethyl)pyrimidine (391 mg, 2.17 mmol, 1.0 eq.) in toluene (15 ml) and the reaction mixture was degassed with nitrogen. BINAP (80 mg, 0.13 mmol, 0.06 eq.) and Pd(OAc)2 (10 mg, 0.04 mmol, 0.02 eq.) were added and the resulting mixture was heated at 120 C. for 16 h. The reaction mixture was filtered through celite and the filtrate was evaporated under reduced pressure to afford the crude product which was purified by column chromatography (silica gel; 0-1% MeOH/MC) to yield the pure desired product as a white solid. Yield: 41% (350 mg, 1.2 mmol).

The synthetic route of 336191-17-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gruenenthal GmbH; US2010/249095; (2010); A1;,
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Brief introduction of 336191-17-4

As the paragraph descriping shows that 336191-17-4 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.336191-17-4,tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate,as a common compound, the synthetic route is as follows.

EXAMPLE 3 N-[2-Amino-5-(2-thienyl)phenyl]-6-(2,8-diazaspiro[4.5]dec-8-yl)nicotinamide 2-Thiophenyl Boc-chloronicotinamide F (60 mg, 0.14 mmol) was dissolved in 1 mL of DMSO and treated with NEt3 (0.100 mL) and tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (50 mg, 0.21 mmol). The mixture was stirred at 90 C. for 18 h, partitioned between EtOAc and saturated NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was dissolved in 1 mL of 1:1 TFA/CH2Cl2, stirred for 5 h and concentrated. Reverse-phase chromatography (10-100% MeCN/water with 0.05% TFA) followed by neutralization with EtOAc/sat’d NaHCO3 extraction and drying (Na2SO4) gave the target spirocyclic compound: 1H NMR (600 MHz, CD3OD): delta 8.73 (s, 1 H), 8.06 (dd, J=8.8, 2.1 Hz, 1 H), 7.45 (s, 1 H), 7.33 (dd, J=8.2, 2.1 Hz, 1 H), 7.21 (dd, J=5.0, 1.2 Hz, 1 H), 7.19 (dd, J=3.5, 0.9 Hz, 1 H), 7.00 (dd, J=5.0, 3.5 Hz, 1 H), 6.88 (d, J=8.5 Hz, 1 H), 6.81 (d, J=9.1 Hz, 1 H), 3.72 (m, 2 H), 3.62 (m, 2 H), 2.94 (t, J=7.3 Hz, 2 H), 2.71 (s, 2 H), 1.68 (t, J=7.0 Hz, 2 H), 1.60 (m, 4 H); MS (ESI+): cal’d [M+H]+ 434.2, obs’d 434.2.

As the paragraph descriping shows that 336191-17-4 is playing an increasingly important role.

Reference£º
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
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