Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19788-37-5,4-(Chloromethyl)-3,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

Example 1293-{[(3,5-Dimethyl-4-isoxazolyl)methyl][(fra?s-4-methylcyclohexyl)carbonyl]amino}-1-(4- pyrazolo[1 ,5-a]pyrimidin-2-ylphenyl)-1 H-pyrazole-4-carboxylic acidTo a stirred suspension of Intermediate 119 (100 mg) in anhydrous DMF (4 mL), was added sodium hydride (60% dispersion in mineral oil) (17 mg). The reaction mixture was stirred at room temperature, under nitrogen for 15 minutes, and then 4-(chloromethyl)-3,5- dimethylisoxazole (154 mg) was added. The reaction mixture was then stirred at 500C1 under nitrogen for 24 h. Water (0.5 mL) was then added to the reaction mixture, and the solvent was removed by evaporation. The residue was then suspended in THF (1 mL) and ethanol (1 mL), and 2M lithium hydroxide solution (2 mL) was added. The reaction was stirred at room temperature for 20 h, before being neutralised with 2M HCI (2 mL) and partitioned between water and dichloromethane. The layers were stirred for 30 minutes, and then separated using a hydrophobic frit. The organic phase was concentrated by evaporation to give a residue which was then purified by ISCO Companion C18 chromatography eluting with a gradient of acetonitrile (containing 0.05% formic acid) in water (containing 0.1% formic acid) to give the title compound. MS calcd for (C3oH3iN7theta4+H)+: 554 MS found (electrospray): (M+H)+= 554, 19788-37-5

As the paragraph descriping shows that 19788-37-5 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/39146; (2007); 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

To a solution of carboxylic acid (5 g) in CH2C12 (400 ml) at 0 C. was added N(OCH3)CH3.HC1 (11.5 g), DEC (15.1 g), HOBt (5.3 g) and NMM (43 ml) and stirred for 14 hr. The mixture was diluted with CH2C12 (100 ml) and the organic layer was washed with 10percent HC1, saturated sodium bicarbonate and brine, dried with Na2SO4, and concentrated in vacuo to afford 5.74 g of crude product (85percent)., 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

Reference£º
Patent; Schering Corporation and Pharmacopeia, Inc.; US2004/147559; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3209-71-0, Isoxazole-3-carboxylic Acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3209-71-0, [0328] To a solution of isoxazole-3-carboxylic acid (100 mg, 0.88 mmol, 1 equiv) in DMF (1 mL), were added HATU (369 mg, 0.97 mmol, 1.1 equiv). The mixture was treated drop wise with DIPEA (365 mg, 2.83 mmol, 3.2 equiv). After stirring at RT for l5minutes, the mixture was treated drop wise with a solution of l-(2,4-bis(trifluoromethyl)benzyl)-lH- pyrazol-4-amine (273 mg, 0.884 mmol, 1 equiv) in DMF (1 mL). The reaction mixture was kept under stirring for 24 h at RT. Product formation was confirmed with TLC & LCMS and reaction mixture was diluted EtOAc (50 mL) & washed with water (50 mL X 2). Organic layer dried over Na2S04 & concentrated under reduced pressure to obtain crude which was further purified by flash column chromatography to obtain pure product N-(l-(2,4- bis(trifluoromethyl)benzyl)-lH-pyrazol-4-yl)isoxazole-3-carboxamide. (40 mg, 11% as off white solid). XH NMR (400 MHz, DMSO-c/6) d 11.06 (s, 1H), 9.14 (d, J= 1.5 Hz, 1H), 8.29 (s, 1H), 8.06 (d, J= 8.3Hz, 2H), 7.76 (s, 1H), 7.05 (d,.7= 8.1Hz, 1H), 6.99 (d, J= 1.7 Hz, 1H), 5.66 (s, 2H).

3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); 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.1072-67-9,5-Methylisoxazol-3-amine,as a common compound, the synthetic route is as follows.

General procedure: To a suspension of 4-hydroxyquinolin-2(1H)-one (7, 1 mmol, 161 mg) in H2O:EtOH(1:1) (8 mL), DBU (20 mol%) was added. The reaction mixture was heated and stirred at 50 C for 15 min to dissolve the reactant. Then, aryl glyoxal monohydrates(1a-h, 1 mmol), 5-methylisoxazol-3-amine (6, 1 mmol, 98 mg) were added to the reaction mixture, which was stirred at the above-mentioned temperature for appropriate times as shown in Table 2. The progress of reaction was controlled by TLC using MeOH:CHCl3/1:10 as eluent. After completion of the reaction, the precipitate was filtered, washed with water and dried to give the desired products 8a-h in high yield (82-89%)., 1072-67-9

As the paragraph descriping shows that 1072-67-9 is playing an increasingly important role.

Reference£º
Article; Aslanpanjeh, Maryam; Poursattar Marjani, Ahmad; Khalafy, Jabbar; Etivand, Nasser; Research on Chemical Intermediates; vol. 46; 1; (2020); p. 165 – 177;,
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14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 9; 1 -(4-(5-(4-( 1 , 1 -Difluoroethyl)-5-phenylisoxazol-3 -yl)- 1 ,2,4-oxadiazol-3 – yl)benzyl)azetidine-3-carboxylic acid, 2,2,2-trifluoroacetic acid salt; 9-A. Methyl S-phenylisoxazole-S-carboxylate; [00179] A solution of S-phenylisoxazole-S-carboxylic acid (0.86 g, 4.55 mmol) in toluene (15.0 mL) and methanol (3 mL) was added a 2M solution of TMS- diazomethane in hexanes (3.1 mL, 6.14 mmol) dropwise at room temperature. The reaction mixture was stirred for 30 minutes and concentrated. The residue was dispersed in methanol (3 mL), stirred for 5 minutes, and filtered to give methyl 5- phenylisoxazole-3-carboxylate (897 mg). The compound had an HPLC ret. time = 2.67 min. : YMC S5 COMBISCREEN 4.6X50 mm; Gradient time: 4 min; Flow rate = 4 ml/min; Solvent A = 10% MeOH – 90% Water – 0.2% H3PO4; Solvent B = 90% MeOH – 10% water – 0.2% H3PO4; Start % B = O; Final % B = 100. LC-MS: M+1 = 204+., 14441-90-8

As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott, Hunter; DYCKMAN, Alaric, J.; PITTS, William, J.; SPERGEL, Steven, H.; WO2010/85581; (2010); 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.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

To a solution of Nl-(lH-l,3-benzodiazol-2-yl)-l-[3-(trifluoromethyl)phenyl]ethane- 1,2-diamine hydrochloride (from Step 9) (0.25 g, 0.701 mmol) in THF (20 mL) was added triethylamine (0.43 mL, d = 0.726 g/cm3, 2.102 mmol) followed by Py-BOP (0.548 g, 1.051 mmol) and the mixture was stirred at ambient temperature. After 15 minutes isoxazole-3-carboxylic acid was added (0.097 g, 0.858 mmol) and the reaction mass was stirred at ambient temperature for 16 h. Then the reaction mass was diluted with 10% aqueous sodium bicarbonate solution (25 mL) and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layer were washed with saturated brine solution (30 mL), dried over sodium sulphate, filtered and concentrated to afford crude product (0.330 g) which was purified by Grace (24.0 g pre-packed cartridge was used) using 6% methanol in chloroform as eluent to afford N- {2-[(lH- 1 ,3-benzodiazol-2-yl)amino]-2-[3-(trifluoromethyl)phenyl]ethyl} – 1 ,2- oxazole-3-carboxamide (0.110 g) as an off- white solid. NMR (400 MHz, AcOH-d4) delta 8.68 (d, 1H, J = 1.2 Hz), 7.86 (t, 2H, J = 7.2 Hz), 7.67 (d, 1H, J = 7.6 Hz), 7.61 (t, 1H, J = 7.6 Hz), 7.37 (dd, 2H, J = 5.6, 2.8 Hz), 7.21 (dd, 2H, J = 6.0, 3.2 Hz), 6.88 (d, 1H, J = 1.6 Hz), 5.40 (dd, 1H, J = 8.0, 4.8 Hz), 4.06 (dd, 1H, J = 14.4, 4.8 Hz), 3.92 (dd, 1H, J = 14.0, 8.8 Hz);MS: m/z 416.1 (M+l)., 3209-71-0

3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ACESION PHARMA APS; S?RENSEN, Ulrik; METE, Anthonio; (122 pag.)WO2019/38315; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

123320-44-5, (3-(Benzyloxy)isoxazol-5-yl)methanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of cyanic bromide (334 mg, 3.15 mmol, 1.05 eq) and (2547) triphenylphosphine (787 mg, 3.00 mmol, 1.00 eq) in dichloromethane (10 mL) was added a solution of (3-benzyl oxyisoxazol-5-yl)methanol (616 mg, 3.00 mmol, 1.00 eq) in (2548) dichloromethane (10mL). The mixture was stirred at 15 C for 1 hour, then 2,3,4,6,7,8,9,10- octahydropyrimido [1,2-a]azepine (480 mg, 3.15 mmol, 1.05 eq) was added at 0 C. The resulting mixture was stirred at 0~15 C for another 14 hr. The solvent was concentrated in vacuum. The residue was further purified by silica gel column chromatography (Petroleum ether: Ethyl acetate = 5:1 to 4:1) to afford 2-(3-benzyloxyisoxazol-5-yl)acetonitrile (320 mg, 1.49 mmol, 50% yield) as a colorless oil. LC/MS (ESI) m/z: 215.0 [M+1] +; 1H-NMR (400MHz, CDCl3) d 7.48 – 7.41 (m, 5H), 6.06 (s, 1H), 5.30 (s, 2H), 3.82 (s, 2H)., 123320-44-5

As the paragraph descriping shows that 123320-44-5 is playing an increasingly important role.

Reference£º
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; DONG, Hanqing; QIAN, Yimin; ZIMMERMAN, Kurt; (1451 pag.)WO2020/51564; (2020); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1072-67-9, 5-Methylisoxazol-3-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Chlorosulfonyl-3-methoxy-thiophene (3.8 g, 17.87 MMOL), the product from step A of Preparative Example 13.29, was dissolved in 100 mL of CH2CI2 and 20 mL of pyridine. 3-Amino-5-methyl-isoxazole (3.5 g, 35. 68 MMOL) was added. The mixture was stirred for 20 h at room temperature, diluted with 100 mL of CH2CI2, and washed with a 0.5 N HCI aqueous solution (50 mL x 2), H20 (50 mL), and brine (50 mL). The organic solution was dried with NA2SO4, and conentrated in vacuo to a brown oil. This oil was dissolved in 100 mL of CH2CI2, washed again with a 0.5 M HCI aqueous solution (30 mL x 3) and brine. After dried over NA2SO4, the organic solution was concentrated in vacuo to a yellow solid, 4.48 g (91 %, MH+= 275.0) of the desired product., 1072-67-9

1072-67-9 5-Methylisoxazol-3-amine 66172, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PHARMACOPEIA, INC.; WO2004/33440; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of YD-014 (320 mg, 1.58 mmol) in anhydrous dichloromethane (10 mL) was added in sequence diisopropylethylamine (DIEA, 305 mg, 2.36 mmol), YD-05 (380 mg, 1.58 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI, 1.2 g, 6.30 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane, and washed in sequence with aqueous sodium hydroxide (2 M), water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography eluting with petroleum ether in ethyl acetate (3:1) to give YD-01 (290 mg, 43% yield) as a light yellow solid.1H-NMR (400 MHz, DMSO-d6) delta 8.23 (d, 111, J=2.6 Hz, 1′-H), 8.15 (dd, 1H, J=9, 2.6 Hz, 2′-H), 7.63-7.60 (m, 2H, 1-H, 5-H), 7.55-7.52 (m, 3H, 2-H, 3-H, 4-H), 7.20 (d, 1H, J=9 Hz, 3′-H), 3.81 (br s, 2H, CH2), 3.39 (br s, 21-1, CH2), 3.20 (br s, 2H, CH2), 2.85 (br s, 2H, CH2), 2.50 (s, 3H, -CH3);13C-NMR (100 MHz, DMSO-d6) delta 168.8, 161.2, 159.6, 153.9, 141.9, 130.2, 129.1, 127.9, 127.3, 126.3, 125.9, 123.7, 120.6, 110.7, 50.1, 49.7, 46.3, 41.3, 11.4; LRMS (API-ES): 427 (M++H)., 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; The University of Hong Kong; US2011/212975; (2011); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

35166-33-7, 3-Hydroxymethyl-5-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2 3-(chIoromethyl)-5-methylisoxazole To a solution of (5-methylisoxazol-3-yl)methanol (370 mg, 3.27 mmol) in DCM (5 mL) was added thionyl chloride (5 mL) dropwise. The resulting mixture was stirred at room temperature for 16 h. The mixture was concentrated to give 3-(chloromethyl)-5-methylisoxazole (350 mg, crude) as brown oil, which was used without purification. LCMS retention time 0.768 min; LCMS MH+ 132.

35166-33-7, The synthetic route of 35166-33-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertrand; GALLASCHUN, Randall; WO2014/143799; (2014); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem