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 (4S)-5-(pyridin-2-ylcarbamoyl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine-7-carboxylic acid (250 mg, 0.768 mmol) in N,N-Dimethylformamide (DMF) (5 mL) under nitrogen at room temp, HATU (584 mg, 1.537 mmol), DIPEA (0.268 mL, 1.537 mmol) and tetrahydrofuran-3-amine (100 mg, 1.153 mmol) were added and the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with ice water and extracted with 2¡Á15 ml of ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulfate and concentrated under reduced pressure to afford crude compound. The crude product was purified by flash column chromatography (100-200 silica gel eluted with 2percent of CH2Cl2/MeOH) to afford (4S)?N5-(pyridin-2-yl)-N7-(tetrahydrofuran-3-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5,7(2H)-dicarboxamide (140 mg, 0.353 mmol, 45.9percent yield) as off white solid. (TLC system: 10percent Methanol in DCM. Rf value: 0.35), LCMS (m/z): 395.23 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta ppm 13.01 (s, 1H), 8.30 (dd, J=4.93, 0.99 Hz, 1H), 7.98-8.17 (m, 2H), 7.93-7.77 (m, 1H), 7.74-7.60 (m, 2H), 7.13 (ddd, J=7.23, 4.93, 0.99 Hz, 1H), 5.48 (dd, J=5.70, 3.07 Hz, 1H), 4.75-4.44 (m, 1H), 4.05-3.55 (m, 4H), 3.23-2.81 (m, 4H), 2.37-2.15 (m, 2H), 2.16-2.05 (m, 1H), 2.16-1.78 (m, 1H).

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

Reference£º
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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 (2-bromo-6,7-dihydrothia.zolo[5 ,4-c]pyridin-5(4H)-yl)( 1 H-indol-2-yl)methanone (0.030 g, 0.083 mmol) was added tetrahydrofuran-3-amine (0.250 mL, 2.90 mmol). The mixture was stirred at 60¡ãC for 96 hours. The mixture was then purified directly by basic reverse phase HPLC to give the desired product (0.0023 g, 7percent yield)Rt (Method A) 3.22 mins, m/z 369 [M+H].

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

Reference£º
Patent; AICURIS GMBH & CO. KG; DONALD, Alastair; URBAN, Andreas; BONSMANN, Susanne; WEGERT, Anita; GREMMEN, Christiaan; SPRINGER, Jasper; (376 pag.)WO2019/86141; (2019); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

Simple exploration of 88675-24-5

As the paragraph descriping 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

Compound TDI01113-4 (200 mg, 0.52 mmol) and tetrahydrofuran-3-amine (54.6 mg, 0.62 mmol) were dissolvedin N,N-dimethylformamide (10 mL), HATU (236 mg, 0.62 mmol) and diisopropylethylamine (268 mg, 2.08 mmol) wereadded, and the reaction was performed at room temperature overnight. Thin layer chromatography (dichloromethane/methanol =10:1) indicated the reaction was complete. Water (60 mL) was slowly added to the reaction solution, a largeamount of solid precipitated and was filtered after being stirred for 30 minutes. The solid was purified by high-performanceliquid chromatography to afford compound TDI01113 (56.2 mg, yellow solid, yield: 23.7percent).1H NMR (400 MHz, DMSO-d6) delta 13.05 (s, 1H), 9.67 (s, 1H), 8.93 (s, 1H), 8.90 (d, J = 6.4 Hz, 1H), 8.42 (dd, J = 8.4, 1.2Hz, 1H), 8.39 (d, J = 6.0 Hz, 1H), 8.23 (s, 1H), 8.18 (s, 1H), 8.10 (s, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.59 (s, 2H), 6.71 (d,J = 6.0 Hz, 1H), 4.51 – 4.45 (m, 1H), 3.91 – 3.85 (m, 2H), 3.77 – 3.71 (m, 1H), 3.66 – 3.63 (m, 1H), 2.24 – 2.15 (m, 1H),1.99 – 1.92 (m, 1H). MS m/z (ESI): 457.0 [M+H].

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

Reference£º
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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 stirred solution of 4-chloro-2-fluoropyridine (0.094 g, 0.574 mmol) inDMSO (2 mL) cooled to 0 ¡ãC under a nitrogen atmosphere was added C52CO3 (0.374g, 1.148 mmol) and the mixture was stirred for 5 mm. Tetrahydrofuran-3-amine(0.05 g, 0.574 mmol) was added and the mixture heated to 90 ¡ãC for 14 h. Water was added and the solution was extracted with ethyl acetate (2 x 20 mL). The combined organic layers were washed with water (2×20 mL). The organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via silica gel chromatography (ethyl acetate and pet ether) to afford 4-chloro-N-(tetrahydrofuran-3-yl)pyridin-2-amine (0.05 g, 0.209 mmol, 36percent yield) as a yellow oil. LCMS (ESI) m/e 199.2 [(M+H) , calcd for C9H12C1N2O, 199.01; LC/MS retention time (method Al); tR = 1.73 mm.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

Analyzing the synthesis route of 88675-24-5

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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.

Compound VIII-5 (400 mg, 0.90 mmol) and 3-aminotetrahydrofuran (IX-8) (48 mg, 1.35 mmol) were dissolved in sec-butanol (3 mL), and the mixture was heated to 125 C for 12 h, until TLC (two Methyl chloride: methanol = 25:1) The starting material VIII-5 was reacted completely, the reaction solution was cooled to room temperature, and the solvent was evaporated to dryness under reduced pressure.200:1 to 50:1), obtained as a white solid, 220 mg, yield: 54.2%

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Reference£º
Patent; China Pharmaceutical University; Xu Yungen; Ji Dezhong; Zhang Lingzhi; Zhu Qihua; Bai Ying; Wu Yaoyao; (41 pag.)CN109608444; (2019); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

To a solution of (4S)-7-(6-methylpyridin-3-yl)-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3- b][l,4]diazepine (300 mg, 1.189 mmol) in tetrahydrofuran (THF) (10 mL) triphosgene (176 mg, 0.594 mmol) was added at 0 C. After 30 min DIPEA (1.038 mL, 5.94 mmol), tetrahydrofuran-3 -amine (155 mg, 1.783 mmol) was added and the reaction mixture was stirred at 70 C for 16 h. The reaction was allowed to reach RT and then poured on cold water (50 mL) and extracted with ethyl acetate (2x 30 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to yield the crude product. The crude product was purified by flash column chromatography (silica-gel: 100- 200 mesh, eluent: 3% MeOH in DCM) to obtained (45)-7-(6-methylpyridin-3-yl)-N- (tetrahydrofuran-3 -yl)-3 ,4-dihydro- 1 ,4-methano pyrido[2,3 -b] [ 1 ,4]diazepine-5(2H)- carboxamide (137.1 mg, 0.371 mmol, 31.2 % yield) as an off white solid. (TLC system: Rf: 0.2, 5%MeOH-DCM), LCMS (m/z): 366.2 [M+H]+.1H NMR (400 MHz, CDC13): delta ppm 10.76 (br t, J=6.80 Hz, 1 H), 8.89 (s, 1 H), 7.99 (dd, J=8.22, 2.08 Hz, 1 H), 7.54 (d, J=7.89 Hz, 1 H), 7.30 – 7.21 (m, 2 H), 5.62 (dd, J=5.81, 2.96 Hz, 1 H), 4.56 (br dd, J=4.82, 1.97 Hz, 1 H), 4.01 – 3.75 (m, 4 H), 3.30 – 3.06 (m, 3 H), 2.99 – 2.91 (m, 1 H), 2.62 (s, 3 H), 2.39 – 2.21 (m, 2 H), 2.07 – 1.85 (m, 2 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 (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

Analyzing the synthesis route of 88675-24-5

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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.

EXAMPLE 1 7,8-Dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine To a solution of 4-chloro-7,8-dimethoxyquinazoline (1.5 g, 6.7 mmol) in DMF (30 mL) was added tetrahydrofuran-3-amine (698 mg, 8.01 mmol), DIPEA (2.3 mL, 13 mmol). Nitrogen was bubbled through the mixture for 5 min. The reaction was then heated at 100¡ã C. for 2 h. The crude mixture was evaporated and the residue was dissolved in ethyl acetate (20 mL), and filtered. The solid was washed with ethyl acetate (10 mL) to give 7,8-dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine 1.4 g (76percent).The racemate of 7,8-dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine 1.4 g was purified by SFC separation and numbered according to the order of elution: [0117] Stereoisomer 1 (first eluting by SFC): 388 mg, [0118] LC-MS (m/z) 276.1 (MH+) tR (minutes, method 3)=1.82. [0119] [alpha]20D=?32 (c=0.10 mg/mL, MeOH) [0120] Stereoisomer 2 (second eluting by SFC): 413 mg [0121] LC-MS (m/z) 276.1 (MH+) tR (minutes, method 3)=1.81. [0122] [alpha]20D=23 (c=0.10 mg/mL, MeOH)

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Reference£º
Patent; Kehler, Jan; Rasmussen, Lars Kyhn; Langgard, Morten; US2015/175584; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem