Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

To a solution of isoxazole-3-carboxylic acid; (119 mg, 1.05 mmol) in DCM (3 mL) was added (COd)2 (190 mg, 1.5 mmol). Then DMF (cat) was added in the mixture. The reaction was stirred at ft for 1 h. A solution of methyl 3-(1-ethyl-4-methyl-1H- benzo [di [1 ,2,3 jtriazol-5-yl)-3-( 1,2,3 ,4-tetrahydroisoquinolin-7-yl)propanoate (80 mg, 0.21 mmol) and TEA (530 mg, 5.25 mmol) in DCM (2 mL) was added to the mixture. The reaction was stirred at ft for another 2 h. The residue was concentrated to give methyl 3-(1- ethyl-4-methyl- 1H-benzo [di [1 ,2,3 jtriazol-5-yl)-3-(2-(isoxazole-3-carbonyl)- 1,2,3,4- tetrahydroisoquinolin-7-yl)propanoate (90 mg, yield: 90%) as white solid. ESI-MS (M+H) :474.2.

3209-71-0, As the paragraph descriping shows that 3209-71-0 is playing an increasingly important role.

Reference£º
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (2018); 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.2510-36-3,3,5-Dimethylisoxasole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

A mixture of 3, 5-dimethyl-isoxazole-4-carboxylic acid (8.1 mg, 0.057 mmol) in dichloromethane (1.5 mL) cooled to [0 oC] was treated with triphenylphosphine (17 mg, 0.063 mmol), and N-chlorosuccinimide (10 mg, 0.074 mmol). This mixture was stirred at [0 oC] for 15 min and at [25 oC] for 20 min. At this time, the reaction was treated with [3-CYCLOPROPYLMETHYL-L- (2-FLUORO-BENZYL)-8- (4-METHYLAMINO-BENZYL)-3,] 7- dihydro-purine-2,6-dione (50 mg, 0.11 mmol). The reaction was then stirred at [25 oC] for 18 h. At this time, the reaction was diluted with dichloromethane (50 mL) and was washed with a saturated aqueous sodium bicarbonate solution [(1 X 10] mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230-400 mesh, 2: 98 methanol/ dichloromethane) afforded 3,5-dimethyl-isoxazole-4-carboxylic acid [{4- [3-] [CYCLOPROPYLMETHYL-L-(2-FLUORO-BENZYL)-2,] 6-dioxo-2,3, 6, 7-tetrahydro-lH-purin-8- ylmethyl] -phenyl} -methyl-amide (7.4 mg, 23.2%) as an off-white solid

2510-36-3, The synthetic route of 2510-36-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); 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

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

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.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

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.13999-39-8,3-Amino-4,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

A solution of 4,5-dimethylisoxazol-3-amine (4.9 g, 44 mmol, 1.0 equiv; CASNo. 13999-39-8, Org. Proc. Res. Dev. 2007, 11, 275-277) and triethylamine (6.4 mL, 46 mmol, 1.05 equiv) in acetonitrile (25 mL) was added portionwise to a 0 0C solution of phenyl chloroformate (5.8 mL, 46 mmol, 1.05 equiv) in THF (100 mL). After stirring at 0 0C for 1 h, the reaction was warmed to room temp overnight. The reaction was concentrated to about one-half the volume and partitioned between ethyl acetate and saturated sodium 20 bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography (20 to 40% ethyl acetate/heptane) to give the title compound as a white solid (8.39 g, 83%). m/z 233 (MH+). 1H NMR (400 MHz, DMSO-d6) delta ppm 10.67 (br. s., 1 H), 7.40 (t, J=8.0 Hz, 2 H), 7.17 – 7.27 (m, 3 H)1 2.12 (s, 3 H), 1.82 (s, 3 H)., 13999-39-8

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; WO2009/127944; (2009); 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.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.,62348-13-4

General procedure: Example 6B (0.2 g, 0.556 mmol) was dissolved in dichloromethane (2.7 ml) and pyridine (0.3 ml) and was treated dropwise with a solution of 3-methylbutanoyl chloride (0.102 ml, 0.835 mmol) in dichloromethane (0.5 ml). The reaction mixture was stirred at 25 C for 2 hours, concentrated, and purified using reverse phase HPLC (Phenomenex Luna C8(2) 5 um IotaOmicronthetaAlpha AXIA column (30mm x 75mm) run with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0- 10.0 min 95% A, 10.0-12.0 min linear gradient 95- 10% A) to afford the title compound.

The synthetic route of 62348-13-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBVIE INC.; SWEIS, Ramzi F.; CURTIN, Michael L.; PLIUSHCHEV, Marina A.; HANSEN, Todd M.; LONGENECKER, Kenton; WO2013/170118; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

42831-50-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.42831-50-5,5-Methylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Thionylchloride (3.53 g, 0.0278 mol) was added to a solutionof 5-Methylisoxazole-4-carboxylic acid (2.7 g, 0.0185 mol) in anhydrous dichloromethane (50 ml) with catalytic drops of DMF. The reaction was heated under reflux for 12 h then followed by removing the solvent under reduced pressure. DCM (20 ml) was added and evaporated 3 times to produce a brown oil that was used directly in the next step.

As the paragraph descriping shows that 42831-50-5 is playing an increasingly important role.

Reference£º
Article; Hamdi, Abdelrahman; Said, Eman; Farahat, Abdelbasset A.; El-Bialy, Serry A.A.; Massoud, Mohammed A.M.; Letters in drug design and discovery; vol. 13; 9; (2016); p. 912 – 920;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem