Tag: 88675-24-5

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, General procedure: A mixture of corresponding 21 (0.48 mmol) and corresponding amine (0.73 mmol) in 2-butyl alcohol (3 mL) was stirred at 125 oC for 12 h. After cooling to room temperature and the solvent was evaporated under reduced pressure. The residue was purification by column chromatography on silica gel to give the derivatives.

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

Reference£º
Article; Ji, Dezhong; Zhang, Lingzhi; Zhu, Qihua; Bai, Ying; Wu, Yaoyao; Xu, Yungen; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 334 – 341;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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, Compound 2 (40 mg, 0.094 mmol, 1.0 eq), 3-aminotetrahydrofuran (16 mg, 0.19 mmol, 2.0 eq), (1[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (43 mg, 0.11 mmol, 1.2 eq) and N,N-diisopropylethylamine (0.033 mL, 0.19 mmol, 2.00 eq) were dissolved in DMF (1 mL) and stirred overnight. The reaction was diluted with ethyl acetate and washed with water (2*). The aqueous layer was back extracted with ethyl acetate and the combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by reverse-phase chromatography afforded 24 mg (52percent) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 9.94 (s, 1H), 8.86 (d, J=6.9 Hz, 1H), 8.72 (d, J=9.4 Hz, 1H), 8.47 (d, J=3.7 Hz, 1H), 8.43 (s, 1H), 8.35 (d, J=5.5 Hz, 1H), 8.17 (d, J=8.5 Hz, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.45 (dd, J=4.1, 8.2 Hz, 1H), 7.34 (d, J=8.1 Hz, 2H), 6.89 (d, J=8.1 Hz, 2H), 5.54 (s, 2H), 4.57-4.49 (m, 1H), 3.93-3.82 (m, 2H), 3.77-3.62 (m, 5H), 2.24-2.14 (m, 1H), 2.02-1.93 (m, 1H); ES-MS [M+1]+: 495.3.

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

Reference£º
Patent; Vanderbilt University; Conn, P. Jeffrey; Lindsley, Craig W.; Hopkins, Corey R.; Felts, Andrew; Bender, Aaron M.; (43 pag.)US2018/57491; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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, To a stirred solution of intermediate 1 (0.21 g, 0.9 mmol) and TEA (0.37 mL, 2.7 mmol) in dry DCM (5 mL) at 0 ¡ãC, triphosgene (0.268 g, 0.90 mmol) was added and stirred for 2 h at RT. Completion of the reaction was monitored by TLC. The reaction mixture was then poured into water (10 mL) and stirred for 10 min. The organic layer was washed with brine (10 mL), dried over anhydrous Na2S04 and evaporated under vacuum. The resulting crude mixture was dissolved in dry DCM (10 mL), then TEA (0.37 mL, 2.7 mmol) followed by tetrahydrofuran-3- amine (0.12 g, 1.35 mmol) were added at 0 ¡ãC under nitrogen atm and stirred for 4 h at RT. Completion of the reaction was moitored by TLC. The mixture was poured into sat. NaHCO3 (10 mL) and the resulting mixture was stirred for 10 min. The organic layer was washed with brine (10 mL), dried over anhydrous Na2S04 and concentrated under vacuum. The resulting crude material was purified by flash chromatography (Biotage Isolera, gradient: 7percent methanol in DCM) to afford the title compound. Yield: 10percent (31.34 mg, white solid). 1H NMR (400 MHz, DMSO-ak) : delta 7.13 (d, J = 7.6 Hz, 1 H), 6.72 (d, J = 7.2 Hz, 1 H), 6.68 (s, 1 H), 6.38 (d, J = 5.6 Hz, 1 H), 4.49 (t, J = 8.4 Hz, 2H), 4.12-4.05 (m, 1 H), 3.79-3.70 (m, 2H), 3.63-3.57 (m, 1 H), 3.40-3.30 (m, 1 H), 3.27-3.20 (m, 4H), 3.12 (t, J = 8.4 Hz, 2H), 2.33-2.25 (m, 3H), 2.21-2.17 (m, 2H), 2.05-1.95 (m, 1 H), 1.79-1.68 (m, 1 H), 1.2 (d, J = 6.4 Hz, 3H). LCMS: (Method A) 346.3 (M+H), Rt. 2.0 min, 96.3percent (Max). HPLC: (Method A) Rt. 2.1 min, 96.3percent (Max).

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

Reference£º
Patent; ASCENEURON S.A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (134 pag.)WO2019/37860; (2019); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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, Step A. (+/-)-N-(2-Nitrophenyl)tetrahvdrofuran-3 -amineA solution of N, jV-diisopropylethylamine (3.20 mL, 18.4mmol), l-fluoro-2- nitrobenzene (0.484 mL, 4.59 mmol), and (+/-)-tetrahydrofuran-3 -amine (400 mg, 4.59 mmol) in rc-butanol (10 mL) was heated to 180 0C in a microwave reactor. After 20 min, the reaction was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography, eluting with a gradient of hexane: EtOAc – 100:0 to 0:100, gave the title compound. MS: mlz = 209 (M + 1).

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

Reference£º
Patent; MERCK & CO., INC.; WO2008/130512; (2008); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

To a solution of (S)-3-(1,4-dimethyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(3-(((R)-2-ethyl-2,3- dihydropyrido[3,4-f][1,4]oxazepin-4(5H)-yl)methyl)-4-methylphenyl)-2,2-dimethylpropanoic acid (100 mg, 0.190 mmol) and tetrahydrofuran-3-amine (19.81 mg, 0.227 mmol) in N,N- dimethylformamide (DMF) (1 mL) was added DIEA (0.099 mL, 0.569 mmol) and HATU (72.1 mg, 0.190 mmol). The mixture was allowed to stir at 25 C for 20 hrs. The reaction was then diluted with water and extracted with ethyl acetate (3×30 mL). The combined organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The residue was dissolved in 3 mL of DMSO, filtered, and purified by reverse phase preparative HPLC under neutral conditions to obtain the title compound (42.9 mg, 0.072 mmol, 37.9 % yield) as a colorless solid. LC-MS m/z 598.5 (M+H)+, 0.88 min (ret. time).1H NMR (400 MHz, METHANOL-d4) deltappm 0.82 – 1.00 (m, 3 H) 1.30 – 1.39 (m, 7 H) 1.39 – 1.68 (m, 3 H) 1.89 – 2.04 (m, 1 H) 2.26 (s, 3 H) 2.68 – 2.90 (m, 5 H) 3.17 – 3.29 (m, 1 H) 3.55 – 3.78 (m, 6 H) 3.81 – 3.99 (m, 2 H) 4.15 – 4.33 (m, 4 H) 4.89 (d, J=7.53 Hz, 1 H) 6.98 (d, J=5.52 Hz, 1 H) 7.04 – 7.19 (m, 3 H) 7.48 (d, J=8.78 Hz, 1 H) 7.69 – 7.80 (m, 1 H) 8.09 (s, 1 H) 8.30 (d, J=5.27 Hz, 1 H)

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CALLAHAN, James Francis; COLANDREA, Vincent J.; COOPER, Anthony William James; GOODWIN, Nicole Cathleen; HUFF, Chelsea Ariane; KARPIAK, Joel; KERNS, Jeffrey K.; NIE, Hong; (404 pag.)WO2018/109647; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

A mixture of (6-(4-((6-chloropyridazin-3-yl)methoxy)-2-oxopyridin-l (2H)-yl)-7,8- dihydronaphthalen-2-yl)methyl methanesulfonate (350 mg, 0.739 mmol), tetrahydrofuran-3- amine (77 mg, 0.886 mmol) and K2CO3 (306 mg, 2.216 mmol) in N, N-dimethylformamide (DMF) (15 mL) was stirred at 80 ¡ãC for 6 hr, then solvent was removed to give the residue which was purified by prep HPLC and chiral prep HPLC to give 4-[(6-chloropyridazin-3- yl)methoxy]-l – {6-[(tetrahydrofuran-3-ylamino)methyl]-3,4-dihydronaphthalen-2-yl}pyridin- 2(lH)-one hydrochloride as a yellow solid (peak 1 , 65 mg, 1 1.2percent yield): 1H NMR (400 MHz, CD3OD) delta ppm 8.05 (d, J = 7.2 Hz, 1H), 7.99 (d, J = 8.8 Hz, 1H), 7.93 (d, J = 8.8 Hz, 1H), 7.41-7.38 (m, 2H), 7.30-7.28 (m, 1H), 6.89-6.87 (m, 1H), 6.80 (s, 1H), 6.63 (d, J = 2.4 Hz, 1H), 5.64 (s, 2H), 4.23-4.21 (m, 2H), 4.06-3.95 (m, 3H), 3.86-3.82 (m, 1H), 3.75-3.72 (m, 1H), 3.1 1 -3.09 (m, 2H), 2.76-2.68 (m, 2H), 2.43-2.41 (m, 1H), 2.15-2.10 (m, 1H); ES- LCMS m/z 465 (M+H), and 4-[(6-chloropyridazin-3-yl)methoxy]-l – {6-[(tetrahydrofuran-3- ylamino)methyl]-3,4-dihydronaphthalen-2-yl}pyridin-2(lH)-one hydrochloride as a yellow solid (peak 2, 49.3 mg, 8.5percent yield): 1H NMR (400 MHz, CD3OD) delta ppm 7.98-7.93 (m, 3H), 7.41-7.38 (m, 2H), 7.30-7.28 (m, 1H), 6.85-6.79 (m, 2H), 6.61 -6.60 (m, 1H), 5.64 (s, 2H), 4.23-4.22 (m, 2H), 4.05-4.00 (m, 3H), 3.87-3.83 (m, 1H), 3.73-3.71 (m, 1H), 3.13-3.09 (m, 2H), 2.73-2.67 (m, 2H), 2.41-2.39 (m, 1H), 2.12-2.10 (m, 1H); ES-LCMS m/z 465 ( +H)+. Chiral HPLC method Instrument: Thar 80 Column: AS 250mm*20mm, 20um Mobile phase: A: Supercritical C02, B: MeOH, A: B =55:45 at 80mL/min Column Temp: 38¡ãC Nozzle Pressure: lOOBar Nozzle Temp: 60¡ãC Evaporator Temp: 20¡ãC Trimmer Temp: 25¡ãC Wavelength: 220nm

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

Reference£º
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHRISTENSEN, IV, Siegfried Benjamin; WU, Chengde; ZHANG, Zhiliu; YU, Haiyu; YUAN, Jiangxing; LIN, Xiaojuan; XU, Shanli; LV, Maoyun; YAO, Chen; LI, Lei; HUANG, Xing; GAO, Min; WO2013/166621; (2013); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

EXAMPLE 44: (2i?)-2-(6-fluoro-3-oxopyrrolo[4,3,2-Je][2,6]naphthyridin- 4(l/f,3/f,5H)-yl)-3-methyl-Lambda/-(tetrahydrofuran-3-yl)butanamide[0410] To an 8 mL scintillation vial equipped for stirring was added (i?)-2-(6-fluoro-3- oxopyrrolo[4,3,2-(ie][2,6]naphthyridin-4(lH,3H,5H)-yl)-3-methylbutanoic acid (15 mg, 0.051 mmol). DMF (0.5 mL), tetrahydrofuran-3 -amine (0.077, 6.7mg), HOBt (11.83 mg, 0.077 mmol), EDC (14.81 mg, 0.077 mmol) and N,N-dimethylpyridin-4-amine (9.44 mg, 0.077 mmol) were added and the solution was stirred at 25¡ãC for 4 h. The reaction mixture was purified via preparative mass trigger LC-MS (AcCN/H2O, 20-50percent). The fractions were collected and lyophilized to afford the title compound as a white solid (7.3mg, 39.3percent). 1H NMR (400 MHz, CD3OD) delta 0.93 (d, J=6.57 Hz, 3 H) 1.04 (dd, J=6.57, 2.78 Hz, 3 H) 1.74 -1.95 (m, 1 H) 2.21 (d, J=7.83 Hz, 1 H) 2.42 – 2.54 (m, 1 H) 3.50 – 3.67 (m, 1 H) 3.69 – 3.97 (m, 3 H) 4.37(td, J=3.85, 1.89 Hz, 1 H) 4.96 – 5.12 (m, 2 H) 5.36 – 5.52 (m, 1 H) 7.86 (s, 1 H) 8.17 (d, J=3.28 Hz, 1 H). [M+H] calc’d for Ci8H2IFN4O3, 361; found, 361.4.

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DONG, Qing; LAWSON, John, David; WALLACE, Michael, B.; KANOUNI, Toufike; WO2010/144486; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

5-fluoro-4-[4-methyl-5-oxo-3-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-2-{[(2S)-4-methylpentan-2-yl]oxy}benzoic acid (Intermediate 82, 150 mg, 395 muiotaetaomicronIota) and tetrahydrofuran-3-amine (44.0 mg, 505 muiotaetaomicronIota) were dissolved in dichloromethane (20 mL). Triethylamine (167 muIota_, 1 .2 mmol) was added, followed by HATU (190 mg, 499 muiotaetaomicronIota). The mixture was stirred at room temperature overnight. The solvent was removed and the mixture was purified using preparative TLC to yield 66mg of desired product (37percent yield).

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Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUeNTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David, B; FERRARA, Steven, James; LIU, Kery; KROeBER, Michael; MERZ, Claudia; NIEHUES, Michael; SCHAeFER, Martina; ZIMMERMANN, Katja; NISING, Carl, Friedrich; (509 pag.)WO2018/77923; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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.

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). The reaction was heated for 4 hours at 250¡ãC in the microwave oven. 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(7H)-one (2 mg, 0.005 mmol) in 3percent yield. 1H NMR (600 MHz, Dimehtyisulfoxide-d6) 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), 4.11 (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). LC-MS: tR = 0.54 min (method 19), m/z = 355.2 [M + H]+.

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

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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.

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

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

Reference£º
Patent; UNILEVER PLC; UNILEVER N.V.; CONOPCO, INC., D/B/A UNILEVER; AU, Van; HARICHIAN, Bijan; CLOUDSDALE, Ian Stuart; BAJOR, John Steven; DICKSON, Jr, John Kenneth; WO2014/139965; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem