Downstream synthetic route of 88675-24-5

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

88675-24-5, Tetrahydrofuran-3-amine is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

88675-24-5, 3-bromo-7-(4-methoxybenzyl)-6-methylimidazo[1 ,5-a]pyrazin-8(7H)-one (60 mg, 0.172 mmol) and tetrahydrofuran-3-amine (0.04 ml, 0.465 mmol) were mixed in NMP (2 mL) and DIPEA (0.23 ml, 1.317 mmol). (1315) The reaction was heated for 4 hours at 250¡ãC in the microwave oven. (1316) The reaction was purified on silica gel, via preparative LC-MS, and preparative TLC (10percent EtOH in ethyl acetate) to give 7-(4-methoxybenzyl)-6-methyl-3-((tetrahydrofuran-3- yl)amino)imidazo[1 ,5-a]pyrazin-8(7/-/)-one (2 mg, 0.005 mmol) in 3percent yield. (1317) 1H NMR (600 MHz, Dimehtylsulfoxide-c/6) delta 8.50 (m, NH), 7.68 (s, 1 H), 7.31 (s, 1 H) 7.22 (d, J = 7.1 Hz, 2H), 6.88 (d, J = 7.1 Hz, 2H), 4.87 (m, 1 H), 4.35 (d, J = 14 Hz, 2H), 4.1 1 (m, 1 H), 4.02 (m, 1 H), 3.92 (m, 1 H), 3.86 (m, 1 H), 3.71 (s, 3H), 2.60 (m, 1 H), 2.5 (m, 1 H) 2.31 (s, 3H). (1318) LC-MS: ?R = 0.54 min (method 19), m/z = 355.2 [M + H]+.

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2018/78042; (2018); A1;,
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Analyzing the synthesis route of 88675-24-5

Big data shows that 88675-24-5 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.

To a solution of butyric acid (253 mg, 2.9 mmol) dissolved in 15 mL of water at ambient temperature, was added N-hydroxysuccinimide (330 mg, 2.9 mmol) followed by EDOHC1 (550 mg, 2.9 mmol). The reaction was stirred for 30 min before 3-aminotetrahydrofuran (250 mg, 2.9 mmol) was added. After 24 h, the solution was extracted with chloroform (3 x 5 mL). The combined chloroform layers were washed with a saturated aqueous solution of sodium bicarbonate (2 x 5 mL), dried with MgS04, filtered and the solvent removed under reduced pressure to afford 22 as a clear oil. Yield: 82.3 mg, 18percent yield. *H NMR (600 MHz, CDC13): delta 5.81 (s, 1H), 4.52-4.46 (m, 1H), 3.88 (ddd, 1H, J=8.0 Hz), 3.77 (dd, 1H, J= 5.4, 9.4 Hz), 3.76- 3.72 (m, 1H), 3.61 (dd, 1H, J=2.5, 9.4 Hz), 2.26-2.18 (m, 1H), 2.10 (t, 2H, J= 7.4 Hz), 1.79-1.71 (m, 1H), 1.61 (sex, 2H, J=7.4 Hz), 0.90 (t, 3H, J=7.4 Hz); 13C NMR (150 MHz, CDC13): delta 172.7, 73.6, 66.8, 50.1, 38.6, 33.2, 19.1, 13.7; ESI MS: Expected [M+H]+: 158.1176, observed: 158.1175; IR (cm 1): 3282, 3068, 2963, 2935, 2873, 1740, 1639, 1540, 1450, 1379, 1286, 1213, 1143, 1063, 908, 802., 88675-24-5

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Reference£º
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; BLACKWELL, Helen; BOURSIER, Michelle, E.; MOORE, Joseph, D.; (110 pag.)WO2017/190116; (2017); A1;,
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Simple exploration of 453-20-3

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453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydrofuran-3-ol (92.5 g, 1.05 mol) indichloromethane (2000 mL) was added pyridinium chlorochromate (454 g, 2.10 mol) and silica gel (500 g). The reaction mixture was heated to 40C. After 16 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford the crude residue. The residue was purified via chromatography on silica gel (methanol/DCM, linear gradient) to afford dihydrofuran-3(2H)-one.

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Reference£º
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; BIENSTOCK, Corey, E.; BUTCHER, John, W.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; DONOFRIO, Anthony; ELLIS, John Michael; FISCHER, Christian; HAIDLE, Andrew, M.; JEWELL, James, P.; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETERSON, Scott, L.; SMITH, Graham Frank; WO2013/52394; (2013); A1;,
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Downstream synthetic route of 86087-23-2

The synthetic route of 86087-23-2 has been constantly updated, and we look forward to future research findings.

86087-23-2, (S)-(+)-3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Take 4-bromo-2-(4-fluorobenzyl)chlorobenzene 148kg,(S)-3-hydroxytetrahydrofuran (45kg) dissolved in 300kg tetrahydrofuranThe ice bath was cooled to 0C and under the protection of nitrogen, a solution of potassium tert-butoxide in tetrahydrofuran was added dropwise.(tert-butanol potassium 56kg, tetrahydrofuran 150kg) 30min drop, drop is completed,5-10 C reaction 1h, after the end of the reaction, add 300kg of water to quench the reaction,Tetrahydrofuran was recovered by distillation and the residue was extracted with 300 kg of ethyl acetate and dried over anhydrous sodium sulfate.After filtration, the solvent was recovered from the filtrate and recrystallized from 70% ethanol to obtain 161 kg of a white solid with a yield of 88%., 86087-23-2

The synthetic route of 86087-23-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Jiangsu Engineering Polytechnic College; Feng Chengliang; Yan Bin; (12 pag.)CN107652278; (2018); A;,
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Downstream synthetic route of 453-20-3

453-20-3, The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The compound tetrahydrofuran-3-ol (1.8 g, 20.0 mmol) was dissolved in DCM (50 mL), cooled to 0 C and then Et3N (3.0 mL, 22.0 mmo1) was added slowly to the reaction followed by MsCl (1.7 mL, 22.0 mmo 1) and a catalytic amount of DMAP were added successively, stirred overnight at room temperature, diluted with DCM (50 mL), washed with water (30 mL ¡Á 2) and separated. The organic phase was dried over anhydrous Na 2 SO 4, Concentration under reduced pressure gave the crude product as a light yellow oil (3.0 g, 90%) which was used directly in the next reaction without further purification.The compound 4-iodo-1H-pyrazole (776 mg, 4.0 mmol) was dissolved in dry DMF (50 mL), cooled to 0 C and then NaH (240 mg, 8.0 mmo 1, 80% NaH / mineral oil) was added and stirring was continued for 1 hour at 0 C. Then a solution of the oil obtained in the previous step (731 mg, 4.4 mmol) in DMF (10 mL) was added dropwise. The reaction was heated to 100 C. and reaction 24 After cooling to room temperature, the reaction was quenched by addition of water (0.5 mL), concentrated under reduced pressure and the residue suspended in DCM (50 mL). The resulting mixture was washed with water (30 mL), separated and the organic phase dried over anhydrous Na 2 SO 4 , Concentrated under reduced pressure to give the title compound as a white solid (1.0 g, 90%).

453-20-3, The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; (88 pag.)CN104119331; (2018); B;,
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Some tips on 453-20-3

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453-20-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

To a solution of 3-tetrahydrofuranol (1 g, 6.5 mmol) in DCM (10 mL) was added triethylamine (1.9 mL, 13.6 mmol). The reaction mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added methanesulfonyl chloride (1.08 mL, 13.6 mmol) at 0C. The reaction mixture was stirred for a further 18 h. The reaction mixture was then quenched by addition of water, and diluted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulphate and concentrated to yield the title compound (1.9 g, 88%). deltaEta (CDC13) 5.32 (m, 1H), 4.10-3.80 (m, 4H), 3.70 (s, 3H), 2.30-2.20 (m, 2H).

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Reference£º
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
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Some tips on 88675-24-5

As the paragraph descriping shows that 88675-24-5 is playing an increasingly important role.

88675-24-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.

a) A solution of TETRAHYDROFURAN-3-AMINE (see W098/08855, 0.500 g, 4.04 mmol) and sodium acetate (0.331 g, 4.04 mmol) in a 1: 3 mixture of methanol and tetrahydrofuran (60 ml) was stirred at room temperature. To this was added (tert-butyl- dimethylsilanyloxy) acetaldehyde (2.112 g, 12.12 mmol) followed by glacial acetic acid (1.456 g, 24.24 mmol) and then sodium triacetoxyborohydride (2.568 g, 12. 12 mmol) was then added in 5 portions over 3 minutes (CAUTION: vigorous effervescence) and the resulting suspension was left to stir at room temperature for 4 hours. The mixture was evaporated under reduced pressure to leave a thick brown paste which was dissolved in dichloromethane (20 ml) and to this was added a solution of ammonia in methanol (7M solution, 25 ml). The mixture was stirred for 10 minutes and then evaporated under reduced pressure to leave an orange paste which was triturated with dichloromethane (50 ml) and filtered through Celite. The mixture was evaporated under reduced pressure to leave a brown gum which was dissolved in methyl tert-butyl ether (3 ML) and then purified by silica gel chromatography using methyl tert-butyl ether as eluent to give N-(2-{ [TERT- butyl (dimethyl) silyl] oxy} ethyl) tetrahydrofuran-3-amine (0.446 g, 48percent yield) as a brown oil: 1H-NMR (CDC13) : 3. 68 (8H, m), 2. 68 (2H, m), 2.04 (1H, m), 1.73 (1H, m), 0. 82 (9H, s), 0.00 (6H, s).

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Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/94410; (2004); A1;,
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Some tips on 88675-24-5

As the paragraph descriping shows that 88675-24-5 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.,88675-24-5

In a 4 mL vial was mixed the 2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (61 mg, 0.25 mmol), tetrahydrofuran-3 -amine (22 mg, 0.25 mmol) and TEA (46 uL, 0.36 mmol) in EtOH (0.3 mL). The reaction was heated to 95 ¡ãC for 2 h before being cooled and concentrated. To the crude residue was added the 2′-bromo-6’H,8’H-spiro[chromane-4,9′-pyrido[3′,2′:4,5]imidazo[2,l-c][l,4]oxazine] (39 mg, 0.10 mmol, Preparation 86), Pd2(dba)3 (9.6 mg, 0.010 mmol), l,3,5,7-Tetramethyl-2,4,8-trioxa-6- phospha-adamantane (6.1 mg, 0.020 mmol) and CS2CO3 (74.8 mg, 0.25 mmol). THF (1 mL) and H20 (0.25 mL) were added, and the reaction was stirred at 60 ¡ãC for 18 h before being cooled to rt and concentrated. The residue was dissolved in 1 : 1 MeOH/DMSO and purified by reverse phase chromatography using a gradient of MeCN (A) and 0.1percent TFA in H20 (B) at a flow rate of 50 mL/min (0- 0.5 min 5percent A, 0.5-8.5 min linear gradient 05-100percent A, 8.7-10.7 min 100percent A, 10.7-11 min linear gradient 100-05percent A) to yield the title compound. (39 mg, 33percent); LC/MS (Table 1, method ai) Rt = 0.61 min; MS 111 ~ 457 (M+H)+. (TNF IC50= B).

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Reference£º
Patent; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (2016); A1;,
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New learning discoveries about 88675-24-5

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.

To a solution of 2-formyl-4,5 -dimethyl-6-(5 -((1 -methylcyclopropyl)methoxy)-2-azabicyclo[4. 1 .Ojheptan-2-yl)nicotinonitrile (compound 5-4 of Scheme 5, 100 mg, 0.295 mmol) in DCE (3 mL) was added tetrahydrofuran-3-amine (25.7 mg, 0.295 mmol) and AcOH (1.687 tL, 0.029 mmol), the mixture was stirred at 40 ¡ãC for 0.5 h. Then sodium triacetoxyborohydride (125 mg, 0.589 mmol) was added and the mixture was stirred at 40 ¡ãC for 16 h. The reactionmixture was quenched with saturated aqeous NaHCO3 (1 0 mL) and the mixture was extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to get the residue, which was further purified by pre-TLC (DCM:MeOH = 10:1) to give the title compound., 88675-24-5

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP and DOHME CORP.; CLAUSEN, Dane James; FELLS, James, I.; KOZLOWSKI, Joseph, A.; LIU, Ping; MAZZOLA, Robert, D., Jr.; (94 pag.)WO2018/226545; (2018); A1;,
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Brief introduction of 88675-24-5

Big data shows that 88675-24-5 is playing an increasingly important role.

88675-24-5, Tetrahydrofuran-3-amine is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 – carbonyl chloride (1 ) (2g, 10.1 mmol) and 3-aminotetrahydrofuran; (29)(1 .0ml, 1 1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid, 88675-24-5

Big data shows that 88675-24-5 is playing an increasingly important role.

Reference£º
Patent; UNILEVER PLC; UNILEVER N.V.; CONOPCO, INC., D/B/A UNILEVER; HARICHIAN, Bijan; CLOUDSDALE, Ian Stuart; YANG, Lin; DICKSON, JR, John Kenneth; WO2014/139952; (2014); A2;,
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