Month: September 2020

21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-l-yl)-phenyl]-2-oxo- oxazolidin-5(5)-yl-methyl}-acetamide (Intermediate IV) (200 mg, 0.57 mmol), in DMF (10 mL), were added isoxazole-S-carboxylic acid (71 mg, 0.63 mmol), EDC (130 mg, 0.68 mmol), HOBt (89 mg, 0.68 mmol) and NMM (0.19 mL, 1.71 mmol) at 0 C. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, DMF was evaporated in vacuo and residue was dissolved in chloroform (50 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.4: 9.6 MeOH: CHCl3) to provide the title compound (156 mg, 67%) as white solid.1H NMR (400 MHz, CDCl3): delta 0.80-0.90 (m, IH), 1.15-1.25 (m, IH), 1.85-2.02 (m, IH), 2.03 (s, 3H), 3.55-3.65 (m, IH), 3.65-3.75 (m, IH), 3.75-3.85 (m, 2H), 4.07 (t, J= 9.0 Hz, IH), 4.08- 4.20 (m, IH), 4.23 (dd, J = 9.1 and 17.6Hz, IH), 4.46 (dd, J = 9.1 and 16.9 Hz, IH), 4.70-4.85 (m, IH), 6.00-6.15 (bs, IH), 6.91 (d, J = 1.7 Hz, IH), 7.15-7.25 (m, 2H), 7.48 (d, J = 8.7 Hz, 2H), 8.33 (t, J= 1.8 Hz, IH) ESIMS (m/z): 411.3 (M+l), 21169-71-1

As the paragraph descriping shows that 21169-71-1 is playing an increasingly important role.

Reference£º
Patent; PANACEA BIOTEC LTD.; JAIN, Rajesh; TREHAN, Sanjay; DAS, Jagattaran; KAUR, Gurmeet; KANWAR, Sandeep; SINGH, Nishan; NANDA, Gurmeet Kaur; MAGADI, Sitaram Kumar; SHARMA, Sudhir Kumar; WO2010/150281; (2010); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 3-phenyl-pyrrolidine (31.6 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H20N2O2: 332.1525, found 332.1539.

1136-45-4, 1136-45-4 5-Methyl-3-phenylisoxazole-4-carboxylic acid 14343, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Amgen Inc.; Biovitrum AB; US2008/21022; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

7063-99-2, Ethyl 5-phenylisoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7063-99-2

A mixture of ethyl 5-phenylisoxazole-3-carboxylate (406 mg, 1.87 mmol) and N-iodosuccinimide (505 mg, 2.24 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with a IN aqueous solution of sodium hydroxide (50 mL), washed with a 2.5% aqueous solution of sodium bisulfite (50 mL), washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (641 mg, 1.87 mmol, 100% yield) as a light yellow oil. The compound had an HPLC retention time = 3.36 minutes (YMC-Combi 4.6 x 50 mm S-5 ODS column) eluting with 10-90% aqueous methanol + 0.2% phosphoric acid over a 4 minute gradient. MS:(M+H) = 343.97. XH-NMR (400 MHz, CDC13) delta ppm 1.47 (t, J=7.1 Hz, 3H), 4.50 (q, J=7.0Hz, 2H), 7.52-7.56 (m, 3H), and 8.05 (m, 2H).

As the paragraph descriping shows that 7063-99-2 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; ZHANG, Yanlei; WO2011/133734; (2011); A1;,
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Isoxazole | C3H3NO – PubChem

5765-44-6, 5-Methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5765-44-6

Sodium (7.36 g, 320 mmol) was reacted with ethanol (368 ml) and then 5-methylisoxazole (26.56 g, 320 mmol) was added to the mixture at 20 C. The mixture wasstirred at 20 oc for 1.5 h and at 0 oc for 1.5h. The white solid was collected by filtration,washed with ether, dried in vacuo to provide the titled compound (1 0.168 g, 30%) as awhite solid.

As the paragraph descriping shows that 5765-44-6 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE LLC; LIN, Hong; MOORE, Michael Lee; QU, Junya; RIVERO, Ralph A.; TEDESCO, Rosanna; YU, Hongyi; LUENGO, Juan Ignacio; WO2013/28263; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.110256-15-0,5-Cyclopropylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed tert-butyl 4-amino-2-benzylpiperidine-1-carboxylate (5 g, 17.22 mmol, 1.00 equiv), dichloromethane (100 mL), TEA (8.707 g, 86.05 mmol, 5.00 equiv), 5-cyclopropyl-1,2-oxazole-3-carboxylic acid (3.957 g, 25.84 mmol, 1.50 equiv), HATU (19.655 g, 51.69 mmol, 3.00 equiv). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 200 mL of EA. The resulting mixture was washed with 3×200 mL of brine (sat.). The organic phase was collected and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). The collected fractions were combined and concentrated under vacuum. The crude product 2.9 g was purified by Prep-SFC with the following conditions (prep SFC 350-2): Column, Chiralpak AD-H, 5x25cm, 5um; mobile phase, CO2(70%), IPA(30%) and DCM/MeOH=1/3:100 ; Detector, uv 210nm yielding two fractions: first peak – cis enantiomers 1.7 g, second peak trans enantiomers 0.6 g. [0279] These products were further purified by SFC. The cis mixtures were purified by Prep-SFC with the following conditions (prep SFC 350-2): Column, Chiralpak AS-H, 5*25cm, 5um; mobile phase, CO2 (70%), IPA (30%) and MeOH (50%); Detector, uv 210nm. This resulted in 820 mg of (2R,4R)-tert-butyl 2-benzyl-4-(5- cyclopropylisoxazole-3-carboxamido)piperidine-1-carboxylate as yellow oil and 870 mg of(2S,4S)-tert-butyl 2-benzyl-4-(5-cyclopropylisoxazole-3-carboxamido)piperidine-1- carboxylate as yellow oil. (2R,4R)-tert-butyl 2-benzyl-4-(5-cyclopropylisoxazole-3- carboxamido)piperidine-1-carboxylate: 1H-NMR (300 MHz, CD3Cl) : 7.26-7.17(m, 5H), 6.88 (d, J = 6.9 Hz, 1H), 6.32(d, J = 0.6 Hz, 1H), 4.38-4.28 (m, 1H), 4.27-4.16 (m, 1H), 4.09-3.98(m, 1H), 3.18-2.99 (m, 2H), 2.82-2.75 (m,1H), 2.12-1.98(m, 2H), 1.91- 1.66 (m, 3H), 1.37(d, J = 2.7 Hz, 9H), 1.18-1.09 (m, 2H), 1.02-0.92 (m, 2H) ppm. LCMS (method A, ESI): RT =1.59 min, m/z =326.0 [M-Boc+H]+. (2S,4S)-tert-butyl 2-benzyl-4- (5-cyclopropylisoxazole-3-carboxamido)piperidine-1-carboxylate: 1H-NMR (300 MHz, CD3Cl) : 7.26-7.17(m, 5H), 6.88(d, J = 6.9 Hz, 1H), 6.32(d, J = 0.6Hz, 1H), 4.38-4.28 (m, 1H), 4.27-4.16 (m, 1H), 4.09-3.98(m, 1H), 3.18-2.99 (m, 2H), 2.82-2.75 (m, 1H), 2.12-1.98(m, 2H), 1.91-1.66 (m, 3H), 1.37(d, J = 2.7 Hz, 9H), 1.18-1.09(m, 2H), 1.02- 0.92(m, 2H) ppm. LCMS (method A, ESI): RT =1.59 min, m/z = 326.0 [M-Boc+H]+. [0280] The trans mixture was purified by Prep-SFC with the following conditions (prep SFC 350): Column, Phenomenex Lux 5u Cellulose-4250*50mm00G-4491-V0- AX664184-1; mobile phase, CO2(50%) and MeOH(50%) ,Detector, uv 220 nm. This resulted in 250 mg of (2S,4R)-tert-butyl 2-benzyl-4-(5-cyclopropylisoxazole-3- carboxamido)piperidine-1-carboxylate as yellow oil and 260 mg of (2R,4S)-tert-butyl 2- benzyl-4-(5-cyclopropylisoxazole-3-carboxamido)piperidine-1-carboxylate as yellow oil. (2S,4R)-tert-butyl 2-benzyl-4-(5-cyclopropylisoxazole-3-carboxamido)piperidine-1- carboxylate: 1H-NMR (300 MHz, CD3Cl) : 7.26-7.17(m, 5H), 6.88(d, J = 6.9 Hz, 1H), 6.32(s, 1H), 4.81-3.91 (m, 3H), 3.08(t, J = 13.5 Hz, 1H), 2.96-2.81(m, 2H), 2.11-2.02(m, 2H), 1.95(d, J = 10.5 Hz, 1H), 1.52-1.22(m, 11H), 1.15-1.05(m, 2H), 1.02-0.92(m, 2H) ppm. LCMS (method A, ESI): RT = 1.58 min, m/z = 448.0 [M+Na]+. (2R,4S)-tert-butyl 2-benzyl-4-(5-cyclopropylisoxazole-3-carboxamido)piperidine-1-carboxylate: 1H-NMR (300 MHz, CD3Cl) : 7.26-7.17(m, 5H), 6.88(d, J = 6.9 Hz, 1H), 6.32(s, 1H), 4.81-3.91 (m, 3H), 3.08(t, J = 13.5 Hz, 1H), 2.96-2.81(m, 2H), 2.11-2.02(m, 2H), 1.95(d, J = 10.5 Hz, 1H), 1.52-1.22(m, 11H), 1.15-1.05(m, 2H), 1.02-0.92(m, 2H) ppm. LCMS (method A, ESI): RT = 1.58 min, m/z = 448.0 [M+Na]+.

110256-15-0, 110256-15-0 5-Cyclopropylisoxazole-3-carboxylic acid 1092113, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna Helen; BELL, Andrew Simon; CHESWORTH, Richard; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (375 pag.)WO2016/40515; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10557-85-4,3,5-Dimethyl-4-iodoisoxazole,as a common compound, the synthetic route is as follows.

To a stirred THF solution (80 mL) of compound 6 (3.62 g, 20.10 mmol) was added dropwise a 2.5 M n-BuLi/hexane solution (8.80 mL, 22 mmol) at 195 K under nitrogen atmosphere. Stirring was continued for 30 min at 195 K, octafluorocyclopentene (C5F8) (2.80 mL, 20.50 mmol) was slowly added and the reaction mixture was stirred for 2 h at this low temperature. The reaction was quenched by water. After being extracted with ether, the organic layer was washed with 1 M aqueous HCl and water. The organic layer dried over anhydrous MgSO4, filtrated, and evaporated. The crude product was purified by column chromatography on silica gel using petroleum ether as the eluent to give 2.80 g compound 7 as pale yellow liquid in 48% yield. 1H NMR (400 MHz, CDCl3): delta 2.26 (s, 3H, -CH3), 2.43 (s, 3H, -CH3); 13C NMR (100 MHz, CDCl3): delta 10.7, 12.2, 99.9, 158.5, 170.6., 10557-85-4

10557-85-4 3,5-Dimethyl-4-iodoisoxazole 613883, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Liu, Gang; Liu, Ming; Pu, Shouzhi; Fan, Congbin; Cui, Shiqiang; Tetrahedron; vol. 68; 10; (2012); p. 2267 – 2275;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

33282-16-5, 5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of compound 15 (1.0 mmol) in dichloromethane (20 ml) was added EDCI¡¤HCl (1.2 mmol) and HOBt (0.1 mmol). Then added corresponding hetroaromatic acids 10a-i, 14a-i and 12a-d (1.0 mmol) and the reaction mixture was stirred at room temperature for 10 h. The reaction was monitored by TLC. After completion of reaction, water was added to reaction mixture and extracted with dichloromethane (2 ¡Á 30 ml). The solvent was evaporated under reduced pressure to afford the crude product which was further purified by column chromatography on silica gel using ethyl acetate and hexane as solvent system to obtain the pure products as solids.

33282-16-5, As the paragraph descriping shows that 33282-16-5 is playing an increasingly important role.

Reference£º
Article; Kamal, Ahmed; Tamboli, Jaki R.; Vishnuvardhan; Adil; Nayak, V. Lakshma; Ramakrishna; Bioorganic and Medicinal Chemistry Letters; vol. 23; 1; (2013); p. 273 – 280;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

123770-62-7, 6.2. tert-Butyl (3aR,5r,6aS)-5-{2-[({[3-(ethoxycarbonyl)-isoxazol-5-yl]methoxy}carbonyl)amino]ethyl}hexahydrocyclo-penta[c]pyrrole-2(1H)-carboxylate; Added slowly to a solution of 0.33 g (1.97 mmol) of ethyl 5-hydroxymethylisoxazole-3-carboxylate and 0.34 ml (1.97 mmol) of N,N-diisopropylethylamine in 10 ml of 1,2-dichloroethane, cooled to 0 C., is 0.43 g (2.16 mmol) of p-nitrophenyl chloroformate in solution in 5 ml of dichloroethane. The mixture is then stirred at room temperature for 2 hours then a solution of 0.5 g (1.97 mmol) of tert-butyl (3aR,5r,6aS)-5-(2-aminoethyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate, obtained in step 6.1., and 0.34 ml (1.97 mmol) of N,N-diisopropylethylamine are added. The mixture is then heated at 70 C. for 3 hours.After returning to room temperature, water is added then the aqueous phase is extracted several times with dichloromethane. The combined organic phases are then successively washed with a 1M aqueous solution of sodium hydroxide (three times) then with a saturated aqueous solution of ammonium chloride (twice). The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. After purification on a silica gel column eluting with a 99/1 then 97/3 mixture of dichloromethane and methanol, 0.44 g of pure product is obtained in the form of an orange oil.LC-MS: M+H=4521H NMR (DMSO) delta(ppm): 7.40 (broad s, 1H), 6.36 (s, 1H), 5.19 (s, 2H), 4.37 (q, 2H), 3.32 (m, 2H), 3.08 (m, 2H), 2.98 (m, 2H), 2.52 (m, 2H), 2.00 (m, 2H), 1.83 (m, 1H), 1.46 (m, 2H), 1.38 (s, 9H), 1.32 (t, 3H), 0.90 (m, 2H).

As the paragraph descriping shows that 123770-62-7 is playing an increasingly important role.

Reference£º
Patent; SANOFI; US2012/136026; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

123770-62-7, In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), commercially available 5-hydroxymethyl-isoxazole-3-carboxylic acid ethyl ester (5.00 g, 26.29 mmol) was dissolved in dry THF (200 ml_). te/t-Butyldimethylsilyl chloride (4.04 g, 26.82 mmol) was added at rt followed by imidazole (1.97 g, 28.92 mmol). The reaction mixture was stirred at rt overnight. Sat. aq. NH4CI (150 ml.) was added followed by EA (100 ml.) and the layers were separated. The aq. layer extracted with EA (2 x 100 ml_). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (9:1 hept-EA) gave the title compound as a light yellow oil: TLC: rf (9:1 hept-EA) = 0.37. LC-MS-conditions 02: tR = 1.14 min; [M+AcCN+H]+ = 327.51.

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/77990; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-methylisoxazole-3-carboxylic acid (3.81 g, 0.03 mol) in 150 mL of toluene was dried via azeotropic distillation of some of the toluene into a two-neck 500 mL round bottom flask fitted with a Dean-Stark trap and a magnetic stirrer. The mixture was allowed to cool to about 90 C, and dimethylformamide, 1 mL, was added. Thionyl chloride (4.8 g, 0.04 mol) was added dropwise over 15 min and the mixture was refluxed for 5 h with continuous stirring. The reaction was allowed to cool to room temperature, and then the solvent was evaporated in vacuo to yield the product, a dark-brown oil, 80%, which crystallized on standing. It was kept under vacuum until further use.

3405-77-4, The synthetic route of 3405-77-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Jackson, Patrice L.; Hanson, Clive D.; Farrell, Alanna K.; Butcher, Raymond J.; Stables, James P.; Eddington, Natalie D.; Scott; European Journal of Medicinal Chemistry; vol. 51; (2012); p. 42 – 51;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem