Category: 16066-84-5

16066-84-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16066-84-5 as follows.

To a solution of tert-butyl N-methylcarbamate (300 mg, 2.29 mmol, CAS16066-84-5) in DMF (10 mL) was added NaH (183 mg, 4.58 mmol, 60% purity) at 0 C. The mixture was stirred at 25 C. for 2 hours. Then non-8-ynyl methanesulfonate (0.5 g, 2.29 mmol, synthesized via Step 1 of Intermediate GQ) in dry DMF (2 mL) was added at 0 C., and then the mixture was stirred at 25 C. for 5 hours. On completion, the mixture was quenched by addtion H2O (30 mL), then extracted with EA (3¡Á50 mL), and the organic phase was concentrated in vacuo to give a residue. The residue was purified by flash silica gel chromatography to give the title compound (410 mg, 70% yield) as colorless oil. 1H NMR (400 MHz, DMSO-d6) delta 3.14 (t, J=7.6 Hz, 2H), 2.75 (s, 3H), 2.74-2.72 (m, 1H), 2.17-2.11 (m, 2H), 1.48-1.42 (m, 4H), 1.39 (s, 9H), 1.35-1.18 (m, 6H).

According to the analysis of related databases, tert-Butyl methylcarbamate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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. 16066-84-5.

To a suspension of sodium hydride (0.056g, 1.41 mmol) in DMF (3 mL) was added a solution of methylcarbamic acid t-butyl ester (0.184 g, 1.41 mmol) in DMF (2 mL). After stirring 1 hr, a solution of 3-(3-chloropropyl)-7-fluoro-1 -phenyl-1 H-4,2,1 – benzoxathiazine 2,2-dioxide (0.25 g, 0.72 mmol) in DMF (4 mL) was added. The mixture was stirred for 2 hr then poured into 2N HCI and extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate then concentrated and the residue purified by Sitheta2 column chromatography (10-35% gradient ethyl acetate/hexane). The purified residue was then dissolved in 5 mL of 2N HCI in ether and 0.1 mL of MeOH and the solution allowed to stand 18 hr whereupon crystals formed. The crystals were collected by filtration to yield 3-(7-fluoro-2,2-dioxido-1 – phenyl-1 H-4,2,1-benzoxathiazin-3-yl)-N-methylpropan-1 -amine hydrochloride (0.159): MS (ES) m/z 350.9;HPLC purity 100.0% at 210-370 nm, 7.4 minutes; Xterra RP18, 3.5 mu, 15O x 4.6 mm column, 1.2 mL/minutes. 85/15-5/95 (ammonium formate buffer pH =3.5/ACN+MeOH) for 10 minutes, hold 4 minutes.HRMS: calculated for Ci7H19FN2O3S + H+, 351.11732; found (ESI, [M+H]+), 351.1161.

The synthetic route of tert-Butyl methylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2008/73956; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16066-84-5, These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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.

tert-butyl [4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl]-methyl-carbamate Under an argon atmosphere 13 mg (0.96 mmol) tert-butyl methyl-carbamate, 11 mg (0.019 mmol) Xantphos, 8.8 mg (0.010 mmol) Pd2 dba3 and 47 mg (0.15 mmol) caesium carbonate were added to 50 mg (0.10 mmol) 1-[6′-chloro-4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 1.00 mL dioxane and the mixture was refluxed for 15 h with stirring. The reaction mixture was evaporated down i. vac. and the residue obtained was used in the next step without further purification. Yield: 59 mg (quantitative) Rt (HPLC): 1.70 min (method B)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16066-84-5.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/59954; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16066-84-5, 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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below.

[00724] Step E: To a stirred solution of (1S,2S,5R)-5-(6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2-phenoxycyclohexan-1-ol (78 mg, 0.18 mmol) and tert-butyl methylcarbamate (121 mg, 0.92 mmol) in 600 muL of dioxane was added Cs2CO3 (120 mg, 0.37 mmol) followed by 2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (34 mg, 0.074 mmol). The reaction mixture was sparged with argon for 5 minutes and then Pd2(dba)3 (34 mg, 0.037 mmol) was added and the vial was capped and heated to 100 C overnight. The reaction mixture was partitioned between dichloromethane (15 mL) and water (15 mL), extracted 3 x 15 mL with dichloromethane, dried over MgSO4, filtered and concentrated. The residue was purified over silica gel (0% to 75% ethyl acetate in hexanes) to afford tert-butyl (1-((1R,3S,4S)-3-hydroxy-4-phenoxycyclohexyl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(methyl)carbamate (30 mg, 31% yield).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16066-84-5, name is tert-Butyl methylcarbamate, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 16066-84-5

A. Methyl-oxiranylmethyl-carbamic acid tert-butyl ester. To a solution of Methyl-carbamic acid tert-butyl ester (1 g, 7.62 mmol) in anhydrous DMF (25 mL) cooled to 0 C. was added sodium hydride (60% dispersion in mineral oil, 0.33 g, 8.38 mmol). After stirring the solution at 0 C. for 30 minutes and 1 hour at room temperature, a solution of 2-Bromomethyl-oxirane (1.04 g, 7.62 mmol) in DMF (2.5 mL) was added dropwise. After stirring the solution at room temperature for 24 hours, the reaction mixture was diluted with ethyl acetate and quenched with water and brine. The ethyl acetate layer was then successively washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield an oil. The oil was purified via flash chromatography (10% ethyl acetate in dichloromethane) to yield the title compound as a clear oil (0.88 g, 62%). 1H NMR (400 MHz, CDCl3) delta 3.78-3.75 (m, 0.5H), 3.56-3.50 (m, 0.5H), 3.21-3.07 (m, 2H), 2.94 (s, 3H), 2.79-2.77 (m, 1H), 2.53-2.51 (m, 1H), 1.47 (s, 9H).

Statistics shows that 16066-84-5 is playing an increasingly important role. we look forward to future research findings about tert-Butyl methylcarbamate.

Reference:
Patent; BIGNAN, Gilles; Gaul, Micheal; Xu, Guozhang; Zhao, Bao-Ping; US2011/200586; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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. 16066-84-5

To a stirred suspension of 6-iodo-3 -((8-methoxy-2-(6-methoxypyridin-3 -yl)-2,3dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-3H-imidazo[4, 5-b]pyridine (0.20 g, 0.38 mmol, Example 1-52-9) in 1,4-dioxane (5 mL) was added tert-butyl-N-methylcarbamate (0.10 g,0.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.018 g, 0.019 mmol), 4,5- bi s(diphenylphosphino)-9, 9-dimethylxanthene (0.044 g, 0.075 mmol) and cesium carbonate (0.18 g, 0.57 mmol). The mixture was degassed under vacuum/backfilled with nitrogen (x3). The mixture was then heated to 115 C. After 18 h, the mixture was allowed to cool to room temperature and was concentrated. Chromatographic purification of the crude product(Biotage, 12 g silica gel column, ethyl acetate/heptane elute) provided semi-pure material. This material was dissolved in dichloromethane (10 mL) and was treated with trifluoroacetic acid (6 mL). The mixture was allowed to stir at room temperature. After 15 mm, the mixture was concentrated. The residue was dissolved in methanol and was neutralized by the addition of solid potassium carbonate. The mixture was filtered and concentrated.Chromatographic purification of the crude product (Biotage, 12 g silica gel column, 0-8% methanol/ethyl acetate elute) provided 0.020 g (12%) of 3-((8-methoxy-2-(6- methoxypyridin-3 -yl)-2,3 -dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-N-methyl-3H- imidazo[4,5-b]pyridin-6-amine as a light yellow solid: ?H NIVIR (400 IVIFIz, CDC13) 8.22 – 8.18 (m, 1H), 7.95 (d, J= 2.5 Hz, 1H), 7.92 (s, 1H), 7.61 (dd, J= 8.6, 2.5 Hz, 1H), 7.28 (d, J= 2.5 Hz, 1H), 6.77 (dd, J= 8.5, 0.7 Hz, 1H), 6.54 – 6.48 (m, 2H), 5.30 (s, 2H), 5.09 (dd, J8.4, 2.5 Hz, 1H), 4.29 (dd, J= 11.6, 2.5 Hz, 1H), 4.06 (dd, J= 11.6, 8.4 Hz, 1H), 3.93 (s, 3H), 3.79 (s, 3H), 2.91 (s, 3H) ppm; (M+1) = 434.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16066-84-5.

Reference:
Patent; GENZYME CORPORATION; KANE, John, L., Jr.; BARBERIS, Claude; CZEKAJ, Mark; ERDMAN, Paul; GIESE, Barret; KOTHE, Michael; LE, Tieu-binh; LIU, Jinyu; MA, Liang; METZ, Markus; PATEL, Vinod; SCHOLTE, Andrew; SHUM, Patrick; WEI, Limli; (408 pag.)WO2017/15267; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics