Month: August 2020

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO393,mainly used in chemical industry, its synthesis route is as follows.,72752-81-9

To a suspension of this pink solid (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAc (3L) was added MeI (238.9g, 1.68 mol) below 20C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether = 1:3) indicated the reaction was complete. Water (2L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 13 (320 g, 93.8%) as a pink solid.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,belong benzoxazole compound

Reference£º
Article; Jonckers, Tim H.M.; Rouan, Marie-Claude; Hache, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 4998 – 5002;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,72752-81-9,Molecular formula: C9H7NO3S,mainly used in chemical industry, its synthesis route is as follows.,72752-81-9

Step 1: To a stirred mixture of methyl 2-mercaptobenzo[d]oxazole-6-carboxylate (5 g, 23.92 mmol) and solidK2CO3 (9.9 g, 71.76 mmol) in anhydrous DMF (50 mL) at rt was added methyl iodide (10.2 g, 71.76 mmol). The mixturewas stirred at rt for 15 h. The reaction mixture was diluted with water then extracted with DCM (3 3). The combinedorganic layers were washed with water and 2 M aq HCl. The organic layer was separated and dried over MgSO4 filtered,and concentrated under reduced pressure to afford methyl 2-(methylthio)benzo[d]oxazole-6-carboxylate (4.24 g, 80%)as a light pink solid that did not require further purification. 1H NMR (300 MHz, CDCl3) delta 8.12 (d, J = 1.1 Hz, 1H), 8.04(dd, J = 1.1,8,3 Hz, 1H), 7.61 (d, J = 8.3 Hz, 1H), 3.95 (s, 3H), 2.79 (s, 3H). LCMS (ESI) m/z 224 (M + H)+.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,belong benzoxazole compound

Reference£º
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,72752-81-9,Molecular formula: C9H7NO3S,mainly used in chemical industry, its synthesis route is as follows.,72752-81-9

To a suspension of compound 5.3 (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAC (3 L) was added MeI (238.9 g, 1.68 mol) below 20 C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether=1:3) indicated the reaction was complete. Water (2 L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 5.4 (320 g, 93.8%) as a pink solid.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,belong benzoxazole compound

Reference£º
Patent; TIBOTEC BVBA; US2010/305073; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,72752-81-9,Molecular formula: C9H7NO3S,mainly used in chemical industry, its synthesis route is as follows.,72752-81-9

General procedure: To a solution of 3-hydroxyanthranilic acid (1.93 g, 12.6 mmol) in saturated HCl MeOH (40 mL) was added p-toluenesulfonic acid (p-TsOH) monohydrate (95 mg, 0.5 mmol). The reaction mixture was stirred at reflux temperature for 12 h. The solvent was evaporated under reduced pressure. The residue was dissolved in AcOEt. The organic layer was washed with saturated KHCO3 solution, water and brine, and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was dissolved in Et2O. The insoluble material was filtered off. The filtrate was concentrated in vacuo. To a solution of methyl 3-hydroxyanthranilate (1.22 g, 7.37 mmol) in CH2Cl2 (10 mL) was added Et3N (1.85 g, 18.25 mmol), followed by dropwise addition of a solution of thiophosgene (923 mg, 8.03 mmol) in CH2Cl2 (2 mL) with stirring at ambient temperature for 5 min. The reaction mixture was concentrated in vacuo. The residue was dissolved in AcOEt. The organic layer was washed with 1-N HCl, water and brine and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure to give a solid, which was crystallized from AcOEt/n-hexane to afford methyl 2-mercaptobenzo[d]oxazole-4-carboxylate (7a) (1.28 g, 84%). 2-bromo-N-(2,6-diisopropylphenyl)hexanamide (2e) was obtained from1 using 6-bromohexanoic acid in place of bromoacetic acid in a manner similar to that described for compound 3a. To a stirred solution of the thus obtained thiol (1.05 g, 5.0 mmol) and 2e (1.77 g, 5.0 mmol) in DMF (20 mL) were added K2CO3 (1.04 g, 7.5 mmol) and 18-crown-6 (132 mg, 0.5 mmol). The reaction mixture was stirred at 80 C for 2 h and diluted with water. The organic layer was extracted with Et2O, washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography and eluted with acetone/n-hexane (1:5) to give a solid, which was recrystallized from acetone/n-hexane to afford 12a (1.84 g, 76%) as colorless needles.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,belong benzoxazole compound

Reference£º
Article; Shibuya, Kimiyuki; Kawamine, Katsumi; Miura, Toru; Ozaki, Chiyoka; Edano, Toshiyuki; Mizuno, Ken; Yoshinaka, Yasunobu; Tsunenari, Yoshihiko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4001 – 4013;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl benzo[d]oxazole-2-carboxylate,27383-86-4,Molecular formula: C9H7NO3,mainly used in chemical industry, its synthesis route is as follows.,27383-86-4

Benzoxazole-2-carboxylic acid hydrazide (4): To a mixture of 3 (0.01 mol) in 10 mL of absolute ethanol and hydrazine hydrate (0.04 mol) was added. Then the reaction mixture was refluxed for 8 h. After completion of the reaction (monitored by TLC), it was then diluted with ice-cold water (20 mL) and the solid obtained was purified by crystallization from ethanol to afford pure product benzoxazole-2-carboxylic acid hydrazide 4. Benzoxazole-2-carboxylic acid N’-acetyl hydrazide (5a-d): To a solution of 4 (0.01 mol) in dioxane (10 mL) corresponding benzoyl chloride (0.01 mol) was added.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl benzo[d]oxazole-2-carboxylate,belong benzoxazole compound

Reference£º
Article; Vodela, Sunil; Mekala, Raghu Vardhan Reddy; Danda, Ravinder Reddy; Kodhati, Venkateshwarlu; Chinese Chemical Letters; vol. 24; 7; (2013); p. 625 – 628;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Methyl benzo[d]oxazole-4-carboxylate, cas is 128156-54-7, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,128156-54-7

General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl benzo[d]oxazole-4-carboxylate,belong benzoxazole compound

Reference£º
Article; Sasmal, Swarnendu; Sen, Indira; Hall, Roger G.; Pal, Sitaram; Tetrahedron Letters; vol. 56; 11; (2015); p. 1374 – 1377;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl benzo[d]oxazole-4-carboxylate,128156-54-7,Molecular formula: C9H7NO3,mainly used in chemical industry, its synthesis route is as follows.,128156-54-7

General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl benzo[d]oxazole-4-carboxylate,belong benzoxazole compound

Reference£º
Article; Sasmal, Swarnendu; Sen, Indira; Hall, Roger G.; Pal, Sitaram; Tetrahedron Letters; vol. 56; 11; (2015); p. 1374 – 1377;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl benzo[d]oxazole-5-carboxylate,924869-17-0,Molecular formula: C9H7NO3,mainly used in chemical industry, its synthesis route is as follows.,924869-17-0

General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl benzo[d]oxazole-5-carboxylate,belong benzoxazole compound

Reference£º
Article; Sasmal, Swarnendu; Sen, Indira; Hall, Roger G.; Pal, Sitaram; Tetrahedron Letters; vol. 56; 11; (2015); p. 1374 – 1377;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl benzo[d]oxazole-7-carboxylate,1086378-35-9,Molecular formula: C9H7NO3,mainly used in chemical industry, its synthesis route is as follows.,1086378-35-9

A solution of methyl benzo[d]oxazole-7-carboxylate (0.5 g, 2.82 mmol), 1-iodo-4-nitrobenzene (0.88 g, 3.53 mmol), lithium tert-butoxide (0.45 g, 5.64 mmol), tetrakis(triphenyl phosphine)palladium(0) (0.16 g, 0.141 mmol) in dioxane under a nitrogen atmosphere was stirred at room temperature for 45 minutes. The resulting thick suspension was diluted with EtOAc, washed with water, organics washed with brine, dried over Na2SO4, decanted and solvent removed under vacuum. The crude was purified by column chromatography on silica gel using 20:1 to 5:1 Hexane:EtOAc as eluent to give methyl 2-(4-nitrophenyl)benzo[d]oxazole-7-carboxylate (0.4 g, 48%). UPLC-MS (Acidic Method, 2 min): rt 1.11 min, m/z 299.0 [M+H]+

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl benzo[d]oxazole-7-carboxylate,belong benzoxazole compound

Reference£º
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R.; GRAHAM, Mark; (46 pag.)WO2020/43880; (2020); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,Methyl benzo[d]oxazole-7-carboxylate,1086378-35-9,Molecular formula: C9H7NO3,mainly used in chemical industry, its synthesis route is as follows.,1086378-35-9

General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl benzo[d]oxazole-7-carboxylate,belong benzoxazole compound

Reference£º
Article; Sasmal, Swarnendu; Sen, Indira; Hall, Roger G.; Pal, Sitaram; Tetrahedron Letters; vol. 56; 11; (2015); p. 1374 – 1377;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem