Category: 21169-71-1

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

A mixture of isoxazole-5-carboxylic acid (2.5 g 22.1 mmol), sodium bicarbonate (5.57 g, 66.32 mmol) and iodomethane (8.26 mL, 132.65 mmol) in DMF (30 mL) was stirred at 25 C. over 19 h. The mixture was diluted in H2O (30 mL) and extracted with ether (2¡Á50 mL). The ether layer washed with brine, dried over MgSO4, filtered, concentrated in vacuo to obtain a crude oil. The crude was further purified by Biotage chromatography (cartridge 40m), eluent EtOAc-Hexanes (1:2), then 100% EtOAc to obtain isoxazole-5-carboxylic acid methyl ester as an amorphous solid (1.2 g, 42.7%). Mass Spectrum (+ESI): 128 (M+H)+., 21169-71-1

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wyeth; US2007/219186; (2007); 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

21169-71-1, General procedure: To a solution of the benzoxazole core (1.0 eq) in DCM (2 mL) was added the carboxylic acid (1.2 eq), EDCI (1.2 eq) and DMAP (0.1 eq). The solution was stirred under nitrogen at 45 C overnight. Work-up 1 (W1): The solution was extended with DCM, a saturated solution of sodium bicarbonate was added and the mixture was extracted three times with DCM. The combined organic layers were then washed with brine, dried with sodium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel, eluting ethyl acetate/cyclohexane 50:50 led to the desired carboxamide.

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ferrins, Lori; Rahmani, Raphael; Sykes, Melissa L.; Jones, Amy J.; Avery, Vicky M.; Teston, Eliott; Almohaywi, Basmah; Yin, JieXiang; Smith, Jason; Hyland, Chris; White, Karen L.; Ryan, Eileen; Campbell, Michael; Charman, Susan A.; Kaiser, Marcel; Baell, Jonathan B.; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 450 – 465;,
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

Compound 85-a (200.00 mg, 1.77 mmol, 1.00 eq) was dissolved in dichloromethane (15.00 mL), and compound 7-a (305.88 mg, 1.95 mmol, 299.88 mL, 1.10 eq), EDCI (464.54 mg, 2.42 mmol, 1.37 eq), HOBt (327.43 mg, 2.42 mmol, 1.37 eq) and NMM (536.75 mg, 5.31 mmol, 583.42 mL, 3.00 eq) were added thereto. The reaction solution was stirred at 10C for 15 hours. After the reaction was completed, the reaction solution was added with water (100 mL), and extracted with dichloromethane (100 mL 3 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?2:1) to give the product of compound 85-b (380.00 mg, yield: 85%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta=8.31 (d, J=1.51 Hz, 1H), 6.75 (d, J=1.51 Hz, 1H), 4.44 (d, J=13.05 Hz, 1H), 4.14-4.22 (m, 2H), 4.08 (d, J=12.55 Hz, 1H), 3.30 (t, J=11.29 Hz, 1H), 3.10 (t, J=11.04 Hz, 1H), 2.57-2.68 (m, 1H), 1.99 (br. s., 2H), 1.77-1.87 (m, 2H), 1.26-1.29 (m, 3H).

21169-71-1, The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; HE, Haiying; WU, Songliang; LUO, Zhi; MOU, Jianfeng; GUO, Fengying; WANG, Chuan; LI, Guoqing; ZENG, Minggao; CHEN, Shuhui; (199 pag.)EP3456711; (2019); 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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

21169-71-1, The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

Boc protected amine Ba (35 mg, 0.044 mmol) is charged in a vial, then a 4 M solution of HCI in dioxane (1 mL, 4 mmol) is added. The solution is stirred at RT for 2 h, after which a precipitate forms. The solution is evaporated to dryness. Acid R2o (6.5 mg, 0.057 mmol, 1 .30 equiv) is dissolved in DMF (0.5 mL), then TEA (30 mu, 0.22 mmol, 5.0 equiv) is added followed by TBTU (17 mg, 0.53 mmol, 1 .2 equiv). The solution is stirred for 15 mins, after which the amine hydrochloride Da is added in DMF (0.5 mL). This solution is stirred at RT for 16 h. Water (2 mL) is added and the organic layer is extracted with EtOAc (3 x 5 mL). The solvent is evaporated and the residue is purified on prep HPLC (MeCN:H20, 0.1 % TFA). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1032. FIA M.S.(electrospray) : 793.4 (M+H)+ Retention time (min) = 5.6 min1H NMR (400 MHz,DMSO-d6): delta 11.03 (s, 1H), 9.13 (d, 1H, J = 6.6 Hz), 8.80 (s, 1H), 8.72 (d, 1H, J = 2.1 Hz), 7.86 (d, 1H, J = 9.1 Hz), 7.11 (d, 1H J = 2 Hz), 7.10 (d, 1H, J = 9.2 Hz), 6.36 (s, 1H), 5.67-5.59 (m, 1H), 5.55-5.44 (m, 2H), 5.14 (dd, 1H, J = 10.1, 8.7 Hz), 4.60-4.51 (m, 2H), 4.36 (dd, 1H, J = 9.9, 7.0 Hz), 4.01 (dd, 1H, J = 11.7, 3.5 Hz), 3.89 (s, 3H), 2.94-2.87 (m, 1H), 2.69-2.56 (m, 2H) , 2.44 (s, 3H), 2.41- 2.31 (m, 2H), 2.07-1.95 (m, 1H), 1.83-1.71 (m, 1H), 1.60-1.35 (m, 13H), 1.33-1.19 (m, 2H), 1.12-0.99 (m, 4H).

21169-71-1, The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); 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

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

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

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.,21169-71-1

To a flask containing 8-[5-(S)-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-1, 2, 4a, 5-tetrahydropyrazino[2, 1-c] [1, 4]benzoxazine-3(4H)-carboxylic acid phenylmethyl ester (EXAMPLE 1, 150 mg, 0.31 mmol) in methanol (5 mL) and methylene chloride (5 mL) is introduced 10% palladium on carbon (70 mg). The mixture is placed under a hydrogen balloon for 17 hours, filtered through celite, and concentrated in vacuo. The residue is dissolved in pyridine (5 mL) followed by the addition of isoxazole-5-carboxylic acid (40 mg, 0.35 mmol), 4-dimethylaminopyridine (5 mg, 0.04 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride(70 mg, 0.35 mmol). The reaction is stirred under an inert atmosphere for 17 hours, diluted with methylene chloride (20 mL), washed with 1N HCl (20 mL) and saline, dried over Na2SO4, concentrated in vacuo and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (97/3). The appropriate fractions are combined (Rf= 0.42, TLC, chloroform/methanol, 90/10) and concentrated in vacuo to give the title compound, HRMS calcd for C21H23N5O6: 441.1648. Found: 441.1658.

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; EP874852; (2004); B1;,
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

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%)., 21169-71-1

21169-71-1 Isoxazole-5-carboxylic acid 2060599, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
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

The title compound N-[5(S)-3-[4-(1-cyanocyclopropan-1-yl)phenyl]-2-oxooxazolidin-5-ylmethyl]isoxazole-5-carboxamide (197 mg) was prepared from 5(S)-aminomethyl-3-[4-(1-cyanocyclopropan-1-yl)phenyl]oxazolidin-2-one (150 mg) and isoxazole-5-carboxylic acid (85.7 mg) in the same manner as described for EXAMPLE 62. [0508] MS (EI+) m/z: 352 (M+). [0509] HRMS (EI+) for C18H16N4O4 (M+): calcd, 352.1172; found, 352.1179.

21169-71-1, The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Fukuda, Yasumichi; US2003/225107; (2003); 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

Example 134 Isoxazole-5-carboxylic acid (1-{4-[3-chloro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-indol-1-yl]-benzylcarbamoyl}-cyclopropyl)-amide To a solution of 12.0 mg (0.106 mmol) of isoxazole-5-carboxylic acid in 2 mL of dichloromethane and 0.2 mL of N,N-dimethylformamide 15 mg (0.036 mmol) of 1-amino-cyclopropanecarboxylic acid 4-[3-chloro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-indol-1-yl]-benzylamide (Reference Example 9), 40.5 mg (0.106 mmol) of HBTU and 28.8 muL (0.43 mmol) of triethylamine were added. The mixture was shaken at room temperature for 18 h, then purified by column chromatography using n-hexane and ethylacetate as eluent to yield 17 mg (91%) of the title compound. MS (EI) 517.1 (MH+)., 21169-71-1

21169-71-1 Isoxazole-5-carboxylic acid 2060599, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Richter Gedeon Nyrt.; Beke, Gyula; Benyei, Gyula Attila; Borza, Istvan; Bozo, Eva; Farkas, Sandor; Hornok, Katalin; Papp, Andrea; Vago, Istvan; Vastag, Monika; US2013/217702; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem