Category: 1228779-96-1

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.

Into a 8-mL round-bottom flask, was placed 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex -l-en-l-yl]methyl]piperazin-l-yl)-2- [l2,l2-difluoro-l4-oxa-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7-tetraen-l0- yl]benzoic acid (20.00 mg, 0.030 mmol, 1.00 equiv), 3-nitro-4-[[(oxan-4-yl)methyl]amino] benzene- l-sulfonamide (11.43 mg, 0.036 mmol, 1.2 equiv), DCM (3 mL), DMAP (14.76 mg, 0.121 mmol, 4 equiv), EDCI (11.58 mg, 0.060 mmol, 2 equiv). The resulting solution was stirred for 12 h at room temperature. The crude product was purified by Prep-HPLC with the following conditions (Waters-2767): Column, X-bridge RP18, 5um, l9* l00mm; mobile phase, 0.03% ammonia in water (0.03% NH4HCO3 & NH4OH) and CH3CN (32% CH3CN up to 52% in 6 min); Detector, UV 254 nm. This resulted in 11.5 mg (39.68%) of 4-(4-[[2-(4- chlorophenyl)-4,4-dimethylcyclohex- l-en- l-yl]methyl]piperazin- l-yl)-2-[l2, 12- difluoro- l4-oxa-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7-tetraen-l0-yl]-N-(3-nitro-4- [[(oxan-4-yl)methyl]amino]benzenesulfonyl)benzamide as a white solid. LC-MS-0: (ES, m/z) M+l=96l.47. 1H-NMR-0(300MHz, d-DMSO, ppm): 511.01 (s, 1H), 8.34-8.33 (d, / =3.0 Hz, 1H), 7.47-7.45 (m, 2H), 7.38-7.35 (m, 2H), 6.82-6.80 (m, 3H), 6.02 (s, 1H), 3.86- 3.51 (m, 7H), 3.39-3.17 (m, 5H), 2.77-2.73 (m, 2H), 2.24-2.20 (m, 6H), 2.00 (s, 2H), 1.42 (m, 2H), 1.30 (s, 1H), 0.95 (s, 6H)., 1228779-96-1

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

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

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

Add Intermediate V4 (46.7g, 63mmol, 1.0eq), Intermediate VM4 (21.7g, 69mmol, 1.1eq) and 800mL dichloromethane to a 1000mL reaction flask, dissolve with stirring, and then add EDCI (14.6g, 76mmol, 1.2 eq) and 4.7g DMAP, the temperature was raised to 30-35 reaction, TLC monitored the reaction.After the reaction was completed, 1L of 10% acetic acid aqueous solution was added and stirred for 30min to separate the organic phase. The organic phase was washed with saturated aqueous sodium bicarbonate solution (300mL ¡Á 1), saturated aqueous sodium chloride solution (300mL ¡Á 1), and dried over anhydrous sodium sulfate. Filter with suction and concentrate the filtrate under reduced pressure to obtain a crude solid. The crude product was recrystallized with 300 mL of ethyl acetate and n-hexane (1: 1),56.8 g of solid product V5 was obtained. Yield: 88%., 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; Nantong Changyou Pharmaceutical Technology Co., Ltd.; Li Zebiao; Chen Dan; Wu Hongdang; Xu Xiaohong; Lin Yanfeng; (9 pag.)CN110878098; (2020); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

To a solution of 2-(lH-pyrrolo[2,3-b]pyridine-5-yloxy)-4-(4-((2-4-chlorophenyl)-4,4- dimethylcyclohex-l-enyl)methyl)piperazin-l-yl)benzoic acid (100 g) in MDC (1500 ml) were added 3-nitro-4-((tetrahydro-2H-pyran-4yl)methylmaino)benzenesulfonamide (71.78 g),DMAP(6.4l g) and EDCI. HC1 (61.16 g) at room temperature and stirred till completion of reaction. After completion of reaction, water was added to the reaction mixture, stirred for 30 minutes and filtered at room temperature. The filtrate was stirred for 30 mins at room temperature and layers were separated. The organic layer (MDC) was distilled atmospherically below at 55 C to obtain residue (diamide content 5%). To residue methanol (1000 inL) was added and temperature was raised to 50-70C and solvent (100 mL) was distilled. To the reaction mass, sodium Hydroxide (10.50 g) solution in methanol was added at 55-60C and stirred for 2 hrs. Reaction mixture was cooled to 40-45C, stirred for 45 mins and filtered. Wet cake was washed with methanol (200 ml). Obtained compound was added to dimethylformamide (300 mL), heated at 50-60C and stirred for 30-50 mins to get clear solution. Methanol (300 mL) was added to the solution at 50-60C and stirred for 30-50 mins. Reaction mixture was cooled to 25- 35C and stirred for 8hrs.The reaction mixture was filtered and solid was washed with mixture of DML: Methanol (1 :3) (100 mL). Wet cake was dried at 25-35C for 1 hr in VTD to obtain sodium salt of Venetoclax (Form AL2 of Venetoclax) 80-90 g. (>53% yield) (diamide content > 0.3% ).1H NMR (300 MHz, Dimethyl sulfoxide d6) 11.53 (br s, 1H), 8.42(br s, 1H), 8.34(t, 1H), 7.95(d, 1H), 7.64(t, 2H), 7.27-7.4l(m, 4H), 6.62-6.78(dd, 2.02), 6.29-6.30(br s, 2H), 3.83-3.88(d, 2H), 3.42(br s, 4H), 3.l9-3.29(m, 6H), 3.0l(br s, 4H), 2.89(s, 1H), 2.74-2.72(m, 3H), 2.20(br s, 6 H), l.95-l.23(m, 9H), 0.92(s, 6H).13C NMR:-l70.89, 156.59, 153.06, 149.85, 146.21, 145.00, 142.54, 135.25, 134.99, 134.45, 133.52, 132.57, 131.26, 130.49, 129.66, 129.61, 128.51, 127.37, 125.48, 123.54, 120.02, 116.22, 113.97, 109.76, 106.55, 100.05, 67.13, 60.27, 52.80, 49.09, 48.31, 47.93, 46.78, 36.25, 35.32, 34.34, 31.24, 30.70, 29.33, 28.37.

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

Reference£º
Patent; ALEMBIC PHARMACEUTICALS LIMITED; TVSK, Vittal; CHUDASAMA, Dinesh; DONTHUKURTHI, Saisuryanarayana; SHAH, Tejas; PATIL, Chetan; VELISOJU, Mahendar; SIRIPRAGADA, Mahender Rao; (28 pag.)WO2019/150253; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

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

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

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

Into a 8-mL round-bottom flask, was placed a solution of 4-(4-[[2-(4-chlorophenyl)- 4,4-dimethylcyclohex-l-en-l-yl]methyl]piperazin- l-yl)-2-[l3-oxa-2,4,l0- triazatricyclo[7.4.0.0A[3,7]]trideca-l,3(7),5,8-tetraen-l0-yl]benzoic acid (35 mg, 0.06 mmol, 1.00 equiv) in dichloromethane (5 mL), 4-dimethylaminopyridine (27.8 mg, 0.23 mmol, 4.00 equiv), 3-nitro-4-[(oxan-4-ylmethyl)amino]benzene-l-sulfonamide (21.7 mg, 0.07 mmol, 1.20 equiv), EDCI (22 mg, 0.11 mmol, 2.00 equiv). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (Waters-2767): Column, X-bridge RP18, 5um, l9* l00mm; mobile phase, 0.03% ammonia in water (0.03% NH4HC03 & NH40H ) and CH3CN (32% CH3CN up to 52% in 6 min); Detector, UV 254 nm. This resulted in 28.3 mg (54%) of 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en- l-yl]methyl]piperazin-l-yl)-N-([3-nitro-4-[(oxan-4-ylmethyl)amino]benzene]sulfonyl)-2-[l3- oxa-2,4,l0-triazatricyclo[7.4.0.0A[3,7]]trideca-l,3(7),5,8-tetraen-l0-yl]benzamide as a yellow solid. LC-MS-: (ES, m/z ): (ES, m/z): M+l=909, R.T= 1.52 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. H-NMR: (CDCl3, 300 MHz) d: 8.70 (s, 1H), 8.46 (m, 2 H), 8.10-8.06 (m, 1 H), 7.89-7.60 (m, 1 H), 7.10 (s, 1 H), 6.94-6.71 (m, 5 H), 6.49 (s, 1 H), 6.16 (s, 1 H), 4.70- 4.65 (m, 2 H), 4.00-4.10 (m, 2 H), 3.67-3. l9(m, 7 H), 3.20-3.00(m, 4 H), 2.78(s, 1 H), 2.58- 2.52(m, 2 H), 2.27-2. l7(m, 3 H), 2.05-l.98(m, 4 H), 1.74-1.70 (m, 3 H), 1.55-1.40 (m, 3H), 0.98 (s, 6H).The measurements of the NMR spectra were done with BrukerAvancelll HD 300MHzwith a probe head of BBOF

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

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); 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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

Compound 10-3 was dissolved in dichloromethane,Add (3 eq) EDCI, (0.3 eq) DMAP,After stirring at room temperature for half an hour, compound 1-5 (0.8 eq) was added.It is then reacted at room temperature for 6-8 hours. After the reaction is completed, the reaction is quenched with water.Extract three times with dichloromethane, and combine the organic phases with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 to 20:1 gave compound S10.

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

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

Compound 13-4 was dissolved in dichloromethane, (3eq) EDCI, (0.3eq) DMAP,After stirring at room temperature for half an hour, compound 1-5 (0.8 eq) was added.It is then reacted at room temperature for 6-8 hours. After the reaction is completed, the reaction is quenched with water.Extract three times with dichloromethane, and combine the organic phases with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 – 30:1 gave compound S13.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

EXAMPLE IG 4- {4-[(4′-chloro- 1 , 1 ‘-biphenyl-2-yl)methyl]piperazin-l -yl} -N-( {3-nitro-4-[(tetrahydro-2H- pyran-4-ylmethyl)amino]phenyl}sulfonyl)-2-phenoxybenzamide; EXAMPLE IE (90 mg), EXAMPLE IF (45 mg), l-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (65 mg), and 4-dimethylaminopyridine (22 mg) were stirred in CH2Cl2 (4 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 20- 100% ethyl acetate/hexanes. H NMR (300MHz, dimethylsulfoxide-d6) delta 11.55 (brs, IH), 8.63 (t, IH), 8.47 (d, IH), 7.75 (d, IH), 7.46 (m, 6H), 7.35 (m, 2H), 7.24 (m, 3H), 7.15 (d, IH), 6.99 (dd, IH), 6.82 (d, 2H), 6.75 (d, IH), 6.38 (d, IH), 3.86 (br d, 2H), 3.49 (m, 2H), 3.37 (br s, 2H), 3.15 (br s, 4H), 2.34 (br s, 4H), 1.91 (br s, 4H), 1.64 (br d, 2H), 1.29 (m, 3H).

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

Reference£º
Patent; ABBOTT LABORATORIES; BRUNCKO, Milan; DING, Hong; DOHERTY, George, A.; ELMORE, Steven, W.; HASVOLD, Lisa; HEXAMER, Laura; KUNZER, Aaron, R.; MANTEI, Robert, A.; MCCLELLAN, William, J.; PARK, Chang, H.; PARK, Cheol-min; PETROS, Andrew, M.; SONG, Xiaohong; SOUERS, Andrew, J.; SULLIVAN, Gerard, M.; TAO, Zhi-fu; WANG, Gary, T.; WANG, Le; WANG, Xilu; WENDT, Michael, D.; WO2010/65865; (2010); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

Compound 26 (0.10 g, 0.18 mmol), Compound 3 (0.055 g, 0.18 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.052 g, 0.27 mmol) and 4-dimethylaminopyridine (DMAP, 0.044 mg, 0.36 mmol) were added to It was stirred at room temperature for 10 h in dichloromethane (20 ml). The reaction was quenched with water (10 mL). Dry over anhydrous sodium sulfate, remove the solvent, The concentrate was subjected to column separation (eluent: ethyl acetate/methanol (v/v) = 30:1), Obtained 90 mg of a yellow solid, The yield was 59%.

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; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Liu Zhiqiang; (35 pag.)CN108658983; (2018); A;,
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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

Compound L, the free base of venetoclax (4-(4-{[2-(4-chlorophenyl)-4,4- dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-({3-nitro-4-[(tetrahydro-2H-pyran-4- ylmethyl)amino]phenyl}sulfonyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide), may be prepared as follows. Compound K (3.39 g), Compound A (1.87 g), 1-ethyl-3-[3- (dimethylamino)propyl]-carbodiimide hydrochloride (2.39 g), and 4-dimethylaminopyridine (1.09 g) were stirred in CH2Cl2 (40 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 25-100% ethyl acetate/hexanes, then 10% methanol/ethyl acetate with 1% acetic acid, to give the product (1.62 g, 32%) as a solid.1H NMR (300 MHz, dimethylsulfoxide-d6) 11.65 (br s, 1H), 8.55 (br s, 1H), 8.04 (d, 1H), 7.89 (dd, 1H), 7.51 (m, 3H), 7.33 (d, 2H), 7.08 (m, 1H), 7.04 (d, 2H), 6.68 (dd, 1H), 6.39 (d, 1H), 6.19 (d, 1H), 3.84 (m, 1H), 3.30 (m, 4H), 3.07 (m, 4H), 2.73 (m, 2H), 2.18 (m, 6H), 1.95 (m, 2H), 1.61 (dd, 2H), 1.38 (m, 2H), 1.24 (m, 4H), 0.92 (s, 6H).

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; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (732 pag.)WO2016/24230; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics