Day: September 28, 2020

A common heterocyclic compound, 851768-35-9,5-Amino-3-methylbenzo[d]isoxazole, 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. 851768-35-9

851768-35-9, Synthesis of 2, 5-dichloro-N- (3-methvl-benzofdlisozazol-5-vl)- benzenesulfonamide, STX 876 (KRB01030) :; To a solution of 2, 5-dichlorobenzenesulphonyl chloride (105 mg, 0.428 mmol) in dichloromethane (3 mL) was added pyridine (100 pL, 1.02 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-3-methyl-1, 2-benzisoxazole (60 mg, 0.41 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a yellow solid (100 mg, 68%), single spot at Rf 0.62 (1: 1 hexane: ethyl acetate). mp 229.4-230. 0C, HPLC purity 94% (tR 2.18 min in 10% water-acetonitrile).’H NMR (CDC13) : 6 7.89 (1H, d, J=2.2 Hz), 7.43 (4H, m), 7.22 (1H, m), 7.09 (1H, s, N-H), 2.54 (3H, s). LCMS: 340.06 (M-CH3). FAB-MS (MH+, C14H10CI2N203S) : calcd 356.9867, found 356.9860

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5-Amino-3-methylbenzo[d]isoxazole,851768-35-9,its application will become more common.

Reference£º
Patent; STERIX LIMITED; WO2005/42513; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5 A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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.

EXAMPLE 27 1-(2,6-DICHLOROBENZOYL)-3-(3-BENZISOXAZOLYL)UREA 3-Aminobenzisoxazole (300 grams) and 2,6-dichlorobenzoyl isocyanate (600 grams) in 50 ml. methylene chloride were stirred at room temperature for one hour. The solvent was then evaporated and the precipitate recrystallized from ethanol. The identity of the product was determined by NMR and IR analysis, yield 500 mg., m.p.=212-215 C. Calculated: C, 51.45; H, 2.59; N, 12.00. Found: C, 51.35; H, 2.40; N, 11.84.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; Eli Lilly and Company; US4336264; (1982); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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. 651780-27-7

Toluene (40 mL) was added to a flask containing ethyl [6-BROM-1,] 2-benzisoxazole-3-carboxylate (3.15 g, 11.7 mmol), tetrakis (triphenylphosphine) palladium [(0)] (835 mg, 0.723 mmol, Strem), cesium carbonate (4.12 g, 12.6 mmol, Aldrich), and 2- (trifluoromethyl) phenylboronic acid (2. [38] g, 12.5 mmol, Aldrich) under argon. This mixture was heated in a 100 C oil bath for 35 hours. The mixture was diluted with EtOAc (250 mL) and washed with 4: 1 water: brine (250 [ML)] followed by brine (250 mL). The organics were filtered through a [1″PLUG] of silica gel and evaporated. Product was split in two, adsorbed onto silica gel, and purified on Biotage Flash 40 M+ silica cartridges using 20% EtOAc in heptane. Yield was 2.08 g of orange solid. [‘H] NMR (400 MHz, DMSO-d6) [5] ppm 1.42 (t, [J=7.] 15 Hz, 3 H) 4.51 (q, [J=7.] 05 Hz, 2 H) 7.52 (d, J=7. 46 Hz, [1] H) 7.51 (d, [J=8.] 09 Hz, 1 H) 7.71 (t, J=7. 57 Hz, [1] H) 7.79 (t, [J=7.] 36 Hz, 1 H) 7.91 (d, [J=7.] 67 Hz, [1] [H)] 7.93 (s, 1 H) 8.14 (d, J=8. 09 Hz, 1 H).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,its application will become more common.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18428; (2004); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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. 36216-80-5

A mixture of benzo[d]isoxazol-3-amine and a sulfonyl chloride in pyridine (0.5 ml.) was stirred at room temperature for 64 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration and a portion of the crude material (50 mg or less) was purified by preparative mass-directed HPLC to give the desired product. See Table B for reaction components and amounts used., 36216-80-5

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, 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. 37924-85-9

Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37924-85-9,3-(Bromomethyl)benzo[d]isoxazole,its application will become more common.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5 A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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.

To a solution of triethylamine (0. 0025 mol) in CH2Cl2 (5 ml) benzoylchloride (0.0025 mol) was added. The mixture stirred at RT and intermediate 3 (0.0025 mol) in CH2C12 (5 ml) added dropwise. The reaction mixture was stirred overnight at RT. The mixture was washed 2 times with H20. The organic layer was separated, dried (MgS04), filtered off and the solvent was evaporated. The residue was purified by column chromatography over silicagel (eluent CH2Cl2) yielding O. OlOg compound 9 (yield of 2%, Melting Point 133C) and a fraction which was further purified by column chromatography over silicagel (eluent hexane/CH2Cl2) yielding 0.225 g of compound 10 (yield of 38%, Melting Point 97C-100C), and 0.100 g of compound 11 (yield of 17%, Melting Point 154C-160C).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/89753; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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. 36216-80-5

Under nitrogen benzo [d] isoxazol-3-amine (3.6g, 26.8mmol) was dissolved in chlorosulfonic acid (15.0mL), heated to 60 stirred overnight.Cooled to room temperature, ice water (20 mL), suction filtered, the filter cake was dried at 60 deg.] C under vacuum to give a white solid (5.0g, 87%).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; Guangdong East sunshine Pharmaceutical Co; Zuo, Yinglin; Zheng, Jinfu; Wen, Liang; Zhang, Min; Wu, Shoutao; Yuan, Xiaofeng; Lin, Runfeng; Wang, Xiaojun; Zhang, Yingjun; (27 pag.)CN104530046; (2016); B;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

37924-85-9 A common heterocyclic compound, 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, 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.

EXAMPLE 18A mixture of 18a (20 mg, 0.060 mmol), 18b (12.7 mg, 0.060 mmol), and potassium carbonate (24.8 mg, 0.18 mmol) in DMF (1 ml) was heated at 50 C for 2h. The reaction solution was purified on RP-HPLC using 10-100% acetonitrile (0.05%TFA) to give 18 as the TFA salt.’HNMR (acetonitrile-d3, 500 MHz) delta = 8.047-8.031 (dd, J = 8.1Hz, IH), 7.738-7.723 (m, 2H), 7.503-7.452 (m, IH), 7.448 (s, IH), 7.399-7.321 (m, 5H), 7.067-7.052 (dd, J – 7.5Hz, IH), 6.173 (s, IH), 4.755 (s, 2H), 3.736-3.701(m, 2H), 3.550-3.450 (m, 2H), 2.800-2.745 (m5 IH), 2.4Gamma3- 2.404 (m, IH), 2.141-2.1 10 (m, IH), 2.036-2.001 (m IH); m z: calcd. for C26H22Cl2N202:465.37; found [M+H+]: 465.00; 466.94.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37924-85-9,3-(Bromomethyl)benzo[d]isoxazole,its application will become more common.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DING, FA-Xiang; JIANG, Jinlong; SHEN, Dong-Ming; SHEN, Hong; SHI, Zhi-Cai; WO2011/137024; (2011); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 16263-54-0,3,6-Dichlorobenzo[d]isoxazole, 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. 16263-54-0

To a solution of benzimidazole-2-one (Aldrich, 1.1 g, 7.5 mmol) in DMF (20 ml) was added 3,6-dichlorobenzoisoxazole (1.5 g, 7.5 mmol) and Cs2CO3 (4.8 g, 15 mmol). The suspension was heated to 15O0C in an oil bath and stirred overnight. The mixture was then cooled to room temperature, diluted with water (30 ml) and stirred in a ice bath for 2 hours. The mixture was then filtered. The solid was washed with water and dried under high vacuum to obtain 2.0 g (93%) of a yellow solid as l-(6-chlorobenzisoxazol-3-yl)benzimidazole-2-one. To a solution of the above product (1.0 g, 3.5 mmol) in DMF (15 ml) was added NaOMe solution in methanol (30% wt/wt, 10 ml). The mixture was heated to 8O0C under vacuum to remove residual methanol and then stirred at 11O0C under nitrogen overnight. The mixture was then cooled to room temperature, diluted with water (50 ml), adjusted to pH 6 with 10% aqueous HCl. The resulting suspension was stirred in an ice bath for 2 hours and filtered. The solid was washed with water and dried in an oven (900C) for 2 hours and then under high vacuum at room temperature for 3 hours to obtain a slightly yellow solid. LC-MS m/e: (M+ 1) = 282, 16263-54-0

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16263-54-0,3,6-Dichlorobenzo[d]isoxazole,its application will become more common.

Reference£º
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

37924-85-9 A common heterocyclic compound, 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, 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.

EXAMPLE 18A mixture of 18a (20 mg, 0.060 mmol), 18b (12.7 mg, 0.060 mmol), and potassium carbonate (24.8 mg, 0.18 mmol) in DMF (1 ml) was heated at 50 C for 2h. The reaction solution was purified on RP-HPLC using 10-100% acetonitrile (0.05%TFA) to give 18 as the TFA salt.’HNMR (acetonitrile-d3, 500 MHz) delta = 8.047-8.031 (dd, J = 8.1Hz, IH), 7.738-7.723 (m, 2H), 7.503-7.452 (m, IH), 7.448 (s, IH), 7.399-7.321 (m, 5H), 7.067-7.052 (dd, J – 7.5Hz, IH), 6.173 (s, IH), 4.755 (s, 2H), 3.736-3.701(m, 2H), 3.550-3.450 (m, 2H), 2.800-2.745 (m5 IH), 2.4Gamma3- 2.404 (m, IH), 2.141-2.1 10 (m, IH), 2.036-2.001 (m IH); m z: calcd. for C26H22Cl2N202:465.37; found [M+H+]: 465.00; 466.94.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37924-85-9,3-(Bromomethyl)benzo[d]isoxazole,its application will become more common.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DING, FA-Xiang; JIANG, Jinlong; SHEN, Dong-Ming; SHEN, Hong; SHI, Zhi-Cai; WO2011/137024; (2011); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics