Category: 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 N-[(7i?, 2S)- 1 – { [ 1 -(3-bromophenyl)- 1 eta-indazol-5-yl]oxy } – 1 -(6-methoxypyridin-3- yl)propan-2-yl]-2,2-difluoropropanamide (37 mg, 68mumol), 3-aminotetrahydrofuran (18 mg, 204mumol), tri-t-butylphosphoniumtetrafluoroborat (8.8 mg, 31 mumol) and trans- bis(acetato)bis[o-(di-o-tolylphosphino)-benzyl]dipalladium(II) (10.3 mg, 14mumol) in 1.5 mL THF was added molybdaenhexacarbonyl (12.5 mg, 47 mumol). The microwave vessel was closed and radiated in a microwave reactor (CEM discover) at 150 W and 125¡ãC for 10 minutes (5 minutes ramp time. Then the solvent was removed i.vac, and the product purified by preparative thin layer chromatography on silica gel (ethyl acetate 100percent) to yield 11 mg (30percent) 3-(5-{[(7i?,25)-2-[(2,2-difluoropropanoyl)amino]-l-(6- methoxypyridin-3 -yl)propyl]oxy } – 1 H-indazol- 1 -y l)-N-(tetrahydrofuran-3 -yl)benzamide . ES+MS: m/z 580 [MH+]1H-NMR (300 MHz, CDCl3); delta = 8.20 (d, IH), 8.08 (dd, IH), 8.02 (s, IH), 7.83 (m, IH), 5 7.71 (m, IH), 7.67 (d, IH), 7.60 (dd, IH), 7.58 (t, IH), 7.16 (dd, IH), 6.99 (d, IH), 6.76 (d, IH), 6.66 (br, IH), 6.43 (br, IH), 5.36 (d, IH), 4.75 (m, IH), 4.40 (dq, IH), 4.01 (m,lH), 3.92 (s, 3H), 3.91 (m, IH), 3.83 (m, 2H), 2.38 (m, IH), 1.95 (m, IH), 1.77 (t, 3H), 1.29 (d, 3H)., 88675-24-5

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

Reference£º
Patent; ASTRAZENECA AB; WO2009/142569; (2009); 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, Example A30 To a solution of Example A3 (2.0 g, 5.7 mmol) in NMP (10 mL) was added tetrahydro-furan-3-ylamine (1.5 g, 17.2 mmol) and DBU (1.7 g, 11.4 mmol). Nitrogen was bubbled through the mixture for 5 min and then it was heated in the microwave at 180¡ã C. for 1 h. The reaction mixture was cooled to RT, poured into water and extracted with EtOAc (3*). The combined organics were washed with brine, dried over Na2SO4, concentrated under reduced pressure and purified by silica gel chromatography to give 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(tetrahydrofuran-3-ylamino)-1,6-naphthyridin-2(1H)-one (0.57 g, 25percent yield). 1H NMR (400 MHz, DMSO-d6): delta 8.39 (s, 1H), 7.66 (s, 1H), 7.27 (d, J=6.4 Hz, 1H), 7.18 (d, J=11.2 Hz, 1H), 6.72 (d, J=9.6 Hz, 1H), 6.33 (s, 1H), 5.31 (s, 2H), 4.46-4.42 (m, 1H), 4.08 (q, J=6.8 Hz, 2H), 3.89-3.81 (m, 2H), 3.75-3.69 (m, 1H), 3.55-3.52 (m, 1H), 2.22-2.17 (m, 1H), 1.83-1.79 (m, 1H), 1.20 (t, J=6.8 Hz, 3H).

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

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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.

To (2-bromo-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)(4-methyl- 1 H-indol-2-yl)methanone (0.035 g, 0.093 mmol) was added tetrahydrofuran-3-amine (0.5 ml, 5.81 mmol). The mixture was stirred at r.t. overnight, then at 70¡ãC for 24h. The mixture was concentrated under reducedpressure, purified by silica gel chromatography, then re-purified by basic reverse phase HPLC to give the desired product (0.003 g, 8percent yield) Rt (Method A) 3.09 mins, m/z 383 [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

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

In a dry flask was placed 8-am ino-6-(3-fluorophenyl)-5-[2-methyl-6-(trifluoromethyl) pyrid in-4- yl]imidazo[i ,2-a]pyrazine-2-carboxylic acid (example 76) (30 mg, 0.07 mmol) then DMF (2 mL) was added and to this HATU (31 mg, 0.08 mmol, 1.2 equiv.) was added. Reaction mixture was stirred for 10 minutes and then DIPEA (0.04 mL, 0.21 mmol, 3 equiv.) followed by 3-aminotetra-hydrofuran (0.06 mg, 0.07 mmol, 1 equiv.) were added and reaction was stirred at r.t. for 48h. Reaction mixture was concentrated under reduced pressure and purified by using flash chromatography (silica gel, DCM/MeOH 0percent to 10percent) to lead to the title compound as a off-white solid, hydrochloride salt (10 mg, 29percent). ESI-MS: 501.20 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 6 8.20 (d, J = 7.2 Hz, 1 H), 8.05 (s, 1 H), 7,88 (s, 2H), 7.76 (s, 1 H), 7.62 (s, 1 H), 7.35 ? 7.25 (m,1 H), 7.20 ?7.11 (m, 2H), 7.08?7.00 (m, 1 H), 4.54 ?4.42 (m, 1 H), 3.91 ?3.79 (m, 2H), 3.75?3.68 (m, 2H), 2.58 (s, 3H), 2.25?2.15 (m, 1 H), 1.95?1.85 (m, 1 H)., 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; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (2019); 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.

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

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

Reference£º
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; BLACKWELL, Helen; BOURSIER, Michelle, E.; MOORE, Joseph, D.; (110 pag.)WO2017/190116; (2017); 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, 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;,
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 (2-bromo-6,7-dihydrothiazolo[5 ,4-c]pyridin-5(4H)-yl)(4-methyl- 1 H-indol-2-yl)methanone (0.035 g, 0.093 mmol) was added tetrahydrofuran-3-amine (0.500 ml, 5.81 mmol). The mixture was stirred at 70¡ãC for 72h then concentrated under reduced pressure, and purified by silica gelchromatography to give the desired product (0.011 g, 33percent yield) Rt (Method A) 3.32 mins, m/z 341 [M+H].

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

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

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).

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

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/94410; (2004); 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

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).

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

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;,
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.

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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem