Tag: 33821-94-2

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

STEP A: Sodium hydride (60% mineral oil dispersion) (26.4 mg, 0.660 mmol) is added at 0C under nitrogen to the solution of (E)-2-amino-7-(4-fluoro-2-pyridin-3-yl-phenyl)-4-methyl-7,8-dihydro- 6H-quinazolin-5-one oxime (Intermediate 1) (0.2 g, 0.550 mmol) in anhydrous DMF (8 mL). After 2 min, 2-(3-bromopropoxy)tetrahydro-2H-pyrane (147 mg, 0.660 mmol) is added and the mixture is heated at 60C for 2 h. The suspension is diluted with H20 and extracted with EtOAc. The organic phase is dried over Na2S04, filtered and concentrated under reduced pressure. The residue is purified by flash column chromatography (eluent DCM/MeOH from 98/2 to 95/5) to give the expected compound (0.253 g, 0.5 mmol, Yield: 91%). LC-MS: method A, rt=l .28 min; (ES+), M+H+= 506.3 1H-NMR (DMSO-d6) delta (ppm): 8.57 (dd, J=4.84, 1.61 Hz, 1 H); 8.53 (dd, J=2.35, 0.88 Hz, 1 H); 7.76 (ddd, J=7.92, 2.35, 1.76 Hz, 1 H); 7.67 (dd, J=8.80, 5.58 Hz, 1 H); 7.45 (ddd, J=7.63, 4.70, 0.88 Hz, 1 H); 7.31 (td, J=8.80, 2.93 Hz, 1 H); 7.1 1 (dd, J=9.54, 2.79 Hz, 1 H); 6.74 (s, 2 H); 4.39-4.62 (m, 1 H); 4.11 (t, J=6.31 Hz, 2 H); 3.59-3.78 (m, 2 H); 3.32-3.48 (m, 2 H); 2.77-3.13 (m, 3 H); 2.55-2.69 (m, 2 H); 2.45 (s, 3 H); 1.87 (quin, J=6.46 Hz, 2 H); 1.27-1.79 (m, 6 H)

As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.

Reference£º
Patent; DAC SRL; AMICI, Raffaella; COLOMBO, Andrea; COURTNEY, Stephen Martin; MERCURIO, Ciro; MONTALBETTI, Christian Aldo Georges Napoleon; MORTONI, Annalisa; VARASI, Mario; WO2013/64919; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of D147 (1 .00 g, 5.02 mmol), 2-(3-bromopropoxy)tetrahydro-2H-pyran (1 .12 g, 5.02 mmol) and K2CO3(1 .39 g, 10.04 mmol) in DMF (20 mL) was heated at 80 C for 3 hrs. The reaction mixture was poured into ice water (60 mL), and extracted with EtOAc (2×30 mL). The organic layer was washed with brine (3×40 mL), dried, filtered and concentrated. The crude was purified by column chromatography on silica gel (PE: EtOAc= 1 : 1 ) to give the title compound as a yellow solid (1 .526 g, yield 89%).

33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DING, Xiao; HO, Ming-Hsun; REN, Feng; YU, Haihua; ZHAN, Yang; (290 pag.)WO2019/12093; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A solution of (Z)-phenyl N’-cyano-N-(3,4-difluorophenyl)carbamimidate (17.69 g, 64.70 mmol), 2-(3-bromopropoxy)tetrahydro-2H-pyran (22.80 g, 17.10 mL, 97.10 mmol) and K2CO3 (17.90 g, 129.00 mmol) in DMF (200 mL) was heated overnight at 85C. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (Hept:EtOAc 90: 10 to 50:50) to give 3-cyano-l-(3,4-difluorophenyl)-2-phenyl-l-(3- tetrahydropyran-2-yloxypropyl)isourea as a white solid (26.90 g, 49%). MS (ES+) m/z: 416.2 [M+H]+.

As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; SARIE, Jerome Charles; VASTAKAITE, Greta; (70 pag.)WO2018/60300; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Potassium hydride (30% w/w in mineral oil, 2.2 g, 16.5 mmol) was suspended in 1 ,2- dimethoxyethane (20.0 mL) and the suspension cooled to 0-5C (ice bath). A solution of 2- methyl-2-(methylsulfonimidoyl)propanenitrile (Int-5, 2.0 g, 13.7 mmol) in 1 ,2-dimethoxyethane (15 mL) was added dropwise over 10 min. The ice bath was removed and the mixture was stirred for 3 h at room temperature. After that, it was cooled again to 0-5C and tetrabutylammonium bromide (235 mg, 730 muiotaetaomicron) followed by 2-(3-bromopropoxy)tetrahydro-2H-pyran (Int-6, 3.95 g, 3.00 mL, 17.7 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. Then, the mixture was poured onto a saturated aqueous solution of sodium hydrogencarbonate (60 mL) and diluted with ethyl acetate (180 mL). After phase separation, the aqueous phase was extraced with ethyl acetate (2 x 50 mL), the combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to afford a yellow biphasic oil as crude product. This was purified by column chromatography (silica gel, 100 g, eluting with ethyl acetate / n- heptane, gradient 40:60 to 100:0) to yield, after drying in vacuo (50C, 5 mbar), the title compound as mixture of diastereoisomers as a colorless viscous oil (3.28 g, 83%). HPLC (method LCMS_gradient) tR = 1.6 min. 1H NMR (CDC13, 400 MHz): delta 1.47-1.60 (m, 4 H), 1.68- 1.77 (m, 1 H), 1.76 (br s, 6 H), 1.78-1.88 (m, 3 H), 3.06 & 3.07 (2s, 3 H, dias ), 3.20-3.41 (m, 2 H), 3.45-3.54 (m, 2 H), 3.79-3.91 (m, 2 H), 4.56-4.60 (m, 1 H). MS (ES+) m/z 205.1 [M+H- (CsHgO)] .

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics