1228779-96-1| Page 4 of 5 | Heterocyclic Building Blocks-Tetrahydropyran

Brief introduction of 1228779-96-1

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1228779-96-1

General procedure: To a solution of appropriate crude acid (1 eq) in CH2Cl2 wereadded EDCI (3 eq), DMAP (0.3 eq) and DIPEA (3 eq). The solutionwas stirred at room temperature for 0.5 h and compound 23 [7] (0.8eq) was added. The resulting mixture was stirred for another 8 hand water was added. The layers were separated, and the aqueouslayer was extracted with CH2Cl2. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under vacuo. The residue was prified by chromatography(CH2Cl2/CH3OH 40:1) to provide target compounds 27a-i,28a-d and 34a-c.

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Luo, Jia; Li, Yang; Tan, Wenfu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 149 – 165;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans 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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

Solution preparation prior to reaction: 10% Acetic Acid:Acetic Acid (37 mL) in water (333 g); 5% NaHCO3:NaHCO3 (9 g) in water (176 g); 5% NaCl:NaCl (9 g) in water (176 g). Compound (N) (13.5 g), DMAP (10.5 g), EDAC (10.7 g) and dichloromethane (300 mL) were combined in a suitable reactor and agitated at 25 C. In a second suitable reactor was charged the Acid (Compound (L), 25 g), Et3N (8.7 g) and dichloromethane (120 mL). The resulting Acid (Compound (L)) solution was slowly charged to the initial suspension of Compound (N) and agitated until reaction completion. N,N-dimethylethylenediamine (9.4 g) was then charged to the reaction mixture with continued agitation. The reaction mixture was warmed to 35 C. and washed with 10% Acetic acid solution (185 mL) twice. The lower organic layer was diluted with more dichloromethane (75 mL) and methanol (12.5 mL). The organic, product layer was then washed with 5% NaHCO3 solution (185 mL) and then washed with 5% NaCl solution (185 mL) at 35 C. The lower, organic layer was separated and then concentrated to 8 vol (256 mL) diluted with methanol (26 mL) and warmed to 38 C. Ethyl Acetate (230 mL) was slowly charged. The resulting suspension was slowly cooled to 10 C. and then filtered. The wet cake was washed twice with a 1:1 mix of dichloromethane and ethyl acetate (2 vol, 64 mL). After drying the wet cake at 90 C., 32 g (84%) of Compound (I) was isolated. 1H NMR (DMSO-d6): delta 0.90 (s, 6H), 1.24 (m, 2H), 1.36 (t, J=6.4 Hz, 2H), 1.60 (m, 2H), 1.87 (m, 1H), 1.93 (s, br, 2H), 2.12 (m, 2H), 2.19 (m, 4H), 2.74 (s, br, 2H), 3.06 (m, 4H), 3.26 (m, 4H), 3.83 (m, 2H), 6.17 (d, J=2.1 Hz, 1H), 6.37 (dd, J=3.4, 1.9 Hz, 1H), 6.66 (dd, J=9.1, 2.2 Hz, 1H), 7.01 (m, 2H), 7.31 (m, 2H), 7.48 (m, 3H), 7.78 (dd, J=9.3, 2.3 Hz, 1H), 8.02 (d, J=2.61 Hz, 1H), 8.54 (d, J=2.33 Hz, 1H), 8.58 (t, J=5.9 Hz, 1H, NH), 11.65 (m, 1H)., 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ABBVIE INC.; Chan, Vincent S.; Christesen, Alan C.; Grieme, Timothy A.; Ku, Yi-Yin; Mulhern, Mathew M.; Pu, Yu-Ming M.; US2014/275540; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Into a 8-mL round-bottom flask, was placed 3- nitro-4-[[(oxan-4-yl)methyl]amino]benzene-l-sulfonamide (6.08 mg, 0.019 mmol, 1 equiv), 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en-l-yl]methyl]piperazin-l-yl)-2-[l4,l4- dioxo-l4lambda6-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7-tetraen-l0- yljbenzoic acid (13 mg, 0.019 mmol, 1 equiv), DCM (0.47 mL, 5.506 mmol, 381.56 equiv), DMAP (9.42 mg, 0.077 mmol, 4 equiv), EDCI (7.39 mg, 0.039 mmol, 2 equiv). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated. The crude product was further purified by Prep-HPLC with the following conditions (Waters I): Column, Xbridge Prep C18 OBD column, 5um, 19* 150mm; mobile phase, Water (0.05% TFA) and CH3CN (46% CH3CN up to 51% in 7 min); Detector, UV 220&254nm. This resulted in 2.5 mg (6.24%) of 4-(4-[[2-(4-chlorophenyl)-4,4- dimethylcyclohex- l-en- l-yl]methyl]piperazin- l-yl)-2-[l4, l4-dioxo- l4lambda6-thia-2,4, 10- triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7-tetraen-10-yl]-N-(3-nitro-4-[[(oxan-4- yl)methyl]amino]benzenesulfonyl)benzamide as a yellow solid. LC-MS-PH-PHNW-4-65-0: (ES, m/z ): M+l=97l.5, R,T= 3.243 min. The measurements of the retention were done with a reversed phase column (C18). Shimadzu LCMS 2020; 50*3.0 Kinetex 2.6u XB-C18, 2.6 microm; Eluent A: water (0.05 % TFA); Eluent B: Acetonitrile; linear gradient

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

The mixture of (S)-2-((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(2- (2- (2-cyclopropylphenyl) pyrrolidin-1-yl) -7-azaspiro [3.5] nonan-7-yl) benzoic acid (2.0 g, 3.56 mmol), triethylamine (1.08 g, 10.68 mmol), 2- (7-Azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (1.62 g, 4.27 mmol) in DCM (100 mL) was stirred for 4 hours at room temperature. Then to the resulting reaction mixture was added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (1.35 g, 4.27 mmol) and DMAP (50 mg, 0.40 mmol). After stirred overnight, the reaction mixture was quenched and washed with NH 4Cl, dried over Na 2SO 4 and concentrated in vacuum. The resulted residue was purified by chromatography column on silica (eluent: PE/EA =1/1, then DCM/MeOH = 60/1 to 40/1), and then the desired compound was obtained (1.3 g, yield: 42.5%). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 11.63 (s, 1H), 11.30 (br, 1H), 8.58 -8.47 (m, 2H), 7.99 (s, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.55 -7.42 (m, 4H), 7.19 -7.08 (m, 2H), 7.04 -6.90 (m, 2H), 6.66 (d, J = 8.8 Hz, 1H), 6.35 (s, 1H), 6.18 (m, 1H), 4.34 -4.08 (m, 1H), 3.85 (d, J = 8.8 Hz, 2H), 3.31 -3.18 (m, 6H), 3.05 -2.93 (m, 4H), 2.67 -2.51 (m, 1H), 2.35 -2.25 (m, 1H), 2.07 -2.01 (m, 1H), 1.95 -1.68 (m, 6H), 1.62 (d, J = 12.8 Hz, 2H), 1.55 -1.21 (m, 9H), 0.92 -0.85 (m, 2H), 0.65 -0.53 (m, 2H). MS (ESI, m/e) [M+1] + 859.8., 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 1228779-96-1

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Some tips on 1228779-96-1

1228779-96-1, The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

A mixture of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4-oxocyclohexyl) benzoic acid (2.0g, 5.71mmol), 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzene sulfonamide (1.8 g, 5.71 mmol), EDCI (1.64 g, 8.57 mmol), DMAP (1.05 g, 8.57 mmol) and TEA (1.15 g, 16.42 mmol) in DCM (20 mL) was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated in vacuum, then purified by chromatography column on silica (eluent: DCM/MeOH = 100/1 to 50/1) to afford 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -N- ((3- nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) phenyl) sulfonyl)-4-(4-oxocyclohexyl) benzamide (1.5 g). MS (ESI) m/e [M+1] + 648.1.

1228779-96-1, The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Downstream synthetic route of 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino )benzenesulfonamide ( 4.73 g) wasdissolved m dichloromethane (124.8 mL) at 34C. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.66 g) and 4-Dimethylaminopyridine(3.33 g) was added to the above solution and stirred for 10 minutes at 35C. A mixture of2-( ( 1H -pyrrolo [2,3-b ]pyridin-5-yl)oxy)-4-( 4-( ( 4′-chloro-5,5-dimethy 1-3,4,5 ,6-tetrahydro[1,1′-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid (7.8 g), triethylamine (3.8 g) indichloromethane (70.2 mL) was stirred for 15 minutes at 35C and it was added dropwise to the above mixture in 15 minutes at the same temperature. The reaction mixturewas stirred for 23 hours at 31 oc and then evaporated the solvent from the reactionmixture to obtain residue. This residue was dissolved in ethyl acetate (80 mL) and washedthe solution with 10% acetic acid (2×80 mL), saturated aqueous sodium bicarbonatesolution (2×80 mL) and then with brine solution (2×80 mL). The separated organic layerwas dried over sodium sulfate and evaporated the solvent completely. The crude productwas combined with acetonitrile (112 mL) and stirred for 2 hour at 34C and filtered thesolid. The solid was dissolved in acetonitrile (60 mL) at 70C and stirred for 1 hour at thesame temperature. The solution was cooled and filtered the solid to obtain titlecompound. Yield: 4.5 g; Purity by HPLC: 99.65%, 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; DR. REDDY?S LABORATORIES LIMITED; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; JURUPULA, Ramprasad; BAIG, Mohammed Azeezulla; CHAKKA, Ramesh; THIPPARABOINA, Rajesh; PEDDY, Vishweshwar; RAO, Pallavi; ORUGANTI, Srinivas; DAHANUKAR, Vilas Hareshwar; (88 pag.)WO2017/212431; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 1228779-96-1

1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

To a solution of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(6- (2-phenylpyrrolidin-1-yl) pyridin-3-yl) benzoic acid (150 mg, 0.32 mmol) in dichloromethane (25 mL) were added o- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (182 mg, 0.48 mmol), triethylamine (1 mL) and 4-Dimethylaminopyridine (40 mg, 0.32 mmol). The mixture was stirred for 0.5 h at r.t. Then 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (199 mg, 0.64 mmol) was added. The reaction was continually stirred overnight at r.t. Afterwards, the mixture was washed with water (15 mL) and the organic layers were dried over anhydrous Na 2SO 4 and concentrated. The residue was further purified by prep-HPLC to give the product (40 mg, 16.2 %). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 12.25 (s, 1H), 11.69 (s, 1H), 8.61 (s, 1H), 8.56 (d, J = 2.0 Hz, 1H), 8.25 (s, 1H), 8.03 (d, J = 2.0 Hz, 1H), 7.82 (d, J = 7.3 Hz, 1H), 7.68-7.46 (m, 4H), 7.38 (d, J = 8.2 Hz, 1H), 7.27 (t, J = 7.3 Hz, 2H), 7.22-7.07 (m, 4H), 6.97 (s, 1H), 6.38 (s, 1H), 6.30 (d, J = 8.2 Hz, 1H), 5.05 (d, J = 7.1Hz, 1H), 3.83 (t, J = 10.0 Hz, 3H), 3.57 (d, J = 9.3 Hz, 1H), 3.31-3.18 (m, 4H), 2.42-2.27 (m, 1H), 1.88-1.78 (m, 4H), 1.60 (d, J = 12.2 Hz, 2H), 1.31-1.14 (m, 2H). MS (ESI, m/e) [M+1] + 774.1

1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

Brief introduction of 1228779-96-1

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Into a 40-mL round-bottom flask, was placed 4-(4- ((4?-chloro-5 ,5-dimethyl-3 ,4,5,6-tetrahydro- [1,1 ?-biphenylj -2-yl)methyl)piperazin- 1 -yl) -2-(3 – methoxy-3 ,4-dthydro-2H-pyrrolo [3?,2?:5,6 jpyrido [2,3-bj [1 ,4joxazepin- 1 (7H)-yl)benzoic acid (50 mg, 0.08 mmol, 1 equiv), DCM (3 mL), 3-nitro-4-[[(oxan-4-yl)methyljaminojbenzene-1- sulfonamide (25.2 mg, 0.08 mmol, 1.00 equiv), EDCI (30.6 mg, 0.16 mmol, 2 equiv), DMAP (39.0 mg, 0.32 mmol, 4 equiv). The resulting solution was stirred for overnight at 25 degrees C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol(10:1). The crude product was purified by Flash-PrepHPLC with the following conditions (IntelFlash-1): Column, C18 reversed phase column; mobile phase, Water (1OMMOL/L NH4HCO3+0.05%NH3.H20) and CH3CN (20.0% CH3CN up to 90.0% in 30 mm); Detector, UV 220 nm. This resulted in 32 mg (40.0%) of 4-(4-((4?-chloro- 5 ,5-dimethyl-3 ,4,5,6-tetrahydro- [1,1 ?-biphenylj -2-yl)methyl)piperazin- 1 -yl) -2-(3 -methoxy-3 ,4- dthydro-2H-pyrrolo [3?,2?:5,6 jpyrido [2,3-bj [1 ,4 joxazepin- 1 (7H)-yl)-N-((3-nitro-4-(((tetrahydro- 2H-pyran-4-yl)methyl)amino)phenyl)sulfonyl)benzamide as a yellow solid. LC-MS: (ES, m/z):M+1=953, R,T= 3.44 mm. ?H NMR (300 MHz, DMSO-d6 ppm) 11.00 (ds, 1H), 8.56 (s, 2H), 7.47-7.44 (m, 2H), 7.36-7.33 (m, 2H), 7.08-7.04 (m, 3H), 6.78-6..65 (m, 2H), 6.57-6.54 (m, 1H),6.43 (s, 1H), 6.04 (s, 1H), 4.05-3.15 (m, 20H), 3.13 (s, 1H), 2.70-2.35 (m, 4H), 2.03 (s, 3H),1.92-1.90 (m, 1H), 1.89-1.87 (m, 2H), 1.7 1-1.67 (m, 2H), 1.53-1.45 (m, 3H), 0.97 (s, 6H)., 1228779-96-1

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 1228779-96-1

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

A mixture of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(5- (2-phenylpyrrolidin-1-yl) pyrazolo [1, 5-a] pyrimidin-2-yl) benzoic acid (250 mg, 0.484 mmol), 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (150 mg, 0.484 mmol), EDCI (196 mg, 0.969 mmol), DMAP (88 mg, 0.727 mmol) and TEA (150 mg, 1.452 mol) in DCM (10 ml) was stirred at ambient temperature for 4 d. The reaction solution was washed with H 2O (10 mL), concentrated, purified by column chromatograph on silica gel (100-200 mesh, eluted with DCM: MeOH = 20: 1) to give a crude product, the crude product was purified by pre-HPLC to give the product (80 mg). 1H NMR (DMSO-d 6) delta ppm: 12.35 (s, 1H), 11.79 (s, 1H), 8.69-8.31 (m, 3H), 8.09 (d, J = 2.4 Hz, 1H), 7.87 (dd, J = 9.2, 2.4 Hz, 1H), 7.77-7.50 (m, 4H), 7.31-7.15 (m, 7H), 6.50-6.43 (m, 2H), 5.15 (s, 1H), 3.89-3.82 (m, 3H), 3.64 (s, 1H), 3.30-3.21 (m, 5H), 2.39-2.33 (m, 1H), 1.93-1.82 (m, 4H), 1.59 (d, J = 12.0 Hz, 2H), 1.29-1.18 (m, 2H). MS (ESI, m/e) [M+1] + 814.1.

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.