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,88675-24-5

Example 26 1-(6-{[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]oxy}pyrimidin-4-yl)-N-(tetrahydrofuran-3-yl)-2,3-dihydro-1H-indole-5-carboxamide; [Show Image] To a mixture of 1-(6-{[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]oxy}pyrimidin-4-yl)-2,3-dihydro-1H-indole-5-carboxylic acid (150 mg) obtained in the below-mentioned Example 75, 3-aminotetrahydrofuran (42.9 muL), and N,N-dimethylformamide (10 mL) were added O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (192 mg) and N-ethyldiisopropylamine (87.8 muL), and the mixture was stirred at room temperature for 1 day. Water was added to the reaction mixture, and the mixture was extracted with a mixed solution of ethyl acetate and tetrahydrofuran. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with 50percent ethyl acetate/hexane to give the title compound (150 mg,87percent) as a white solid. 1H-NMR (300 MHz, CDCl3)delta:1.20 (t, J=7.6 Hz, 3 H), 1.72 – 2.00 (m, 3 H), 2.04 – 2.16 (m, 2 H), 2.29 – 2.43 (m, 1 H), 2.47 (q, J=7.6 Hz, 2 H), 3.27 (t, J=8.5 Hz, 2 H), 3.50 – 3.64 (m, 2 H), 3.76 – 3.96 (m, 3 H), 3.97 – 4.07 (m, 3 H), 4.23 – 4.35 (m, 2 H), 4.67 – 4.80 (m, 1 H), 5.34 – 5.46 (m, 1 H), 5.97 (s, 1 H), 6.19 (d, J=7.2 Hz, 1 H), 7.58 (dd, J=8.5, 1.5 Hz, 1 H), 7.65 (d, J=1.5 Hz, 1 H), 8.19 (s, 2 H), 8.41 (d, J=8.5 Hz, 1 H), 8.51 (s, 1 H).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); 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

A suspension of (+/-)-tetrahydro~3-furanamine (1.1 g, 8.90 mmol, Small Molecules Inc., NJ, USA), 1 ,1-dimethyIethyl (2-bromoethy.)carbamate (1.995 g, 8.90 mmol), and potassium carbonate (3.69 g, 26.7 mmol) in N.N-dimethylformannide (15 mL) was maintained at 50 ¡ãC in a sealed pressure vessel for 16 hours. The mixture was cooled, diluted with ethyi acetate, and poured into water. The organic layer was washed twice with 5percent LiCI (aqueous), dried over sodium sulfate, and taken to a residue under reduced pressure to afford 1 ,1-dimethylethyl [2-(tetrahydro-3- furanylamino)ethyl]carbamate (1.33 g, 5.77 mmol, 65percent yield, roughly 50percent purity) as a clear oil used immediately in the subsequent transformation

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

Reference£º
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John, G.; CHONG, Pek, Yoke; FANG, Jing; GARRIDO, Dulce, Maria; PEAT, Andrew, James; PRICE, Daniel, J.; SHOTWELL, John, Brad; TAI, Vincent; ZHANG, Huichang; WO2011/41713; (2011); A2;,
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, General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

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

Reference£º
Patent; MASARYKOVA UNIVERZITA; BRYJA, Vitezslav; JANOVSKA, Pavlina; GREGOROVA, Michaela; NEMEC, Vaclav; KHIRSARIYA, Prashant; PARUCH, Kamil; (171 pag.)WO2019/185631; (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

To a stirred solution of 4,6-dichloropyrimidine (0.3 g, 2.014 mmol) in DMF (10 mL) at 0 ¡ãC, was added NaH (0.242 g, 6.04 mmol). After stirred for 5 mm, tetrahydrofuran-3-amine (0.175 g, 2.014 mmol) was added and stirred overnight atRT The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with DCM (80 mL). The organic layer was washed with brine (40 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 6-chloro-N- (tetrahydrofuran-3-yl)pyrimidin-4-amine (0.3 g, 0.872 mmol, 43percent yield) as ayellowish semi-solid. LCMS (ESI) m/e 200.4 [(M+H), calcd for C8H11C1N3O,200.11; LC/MS retention time (method B): tR = 0.60 mm., 88675-24-5

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

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

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, General procedure: All reactions were carried out in vials under nitrogen atmosphere. Step 1: A solution of compound 15 (125?mumol, 1.0?equiv) and compound 16 (125?mumol, 1.0?equiv) in MeOH (0.3?M) was treated with NaHCO3 (250?mumol, 2.0?equiv) and stirred for 16?h at 30?¡ãC. The reaction was then treated with NaBH4 (125?mumol, 1.0?equiv) and stirred for 3?h (LCMS check). The reaction mixture was filtered and concentrated. The crude amine was suspended in 1?N NaOH (1?mL) and extracted with dichloromethane (3?¡Á?1?mL). The organics were pooled, dried (Na2SO4) and evacuated to afford 18. Step 2: A solution of 17 (75?mumol, 0.60?equiv) in DMF (0.1?M) was treated with HATU (75?mumol, 0.60?equiv) followed by the crude amine 18 (125?mumol, 1.0?equiv) and iPr2NEt (225?mumol, 1.8?equiv). The reactions were concentrated and purified directly by reversed phase preparative HPLC using a C18 column and eluting with acetonitrile?water (0.225percent formic acid or pH?=?10 NH4OH) gradient. All compounds were deemed greater than 95percent purity by LCMS and HPLC. #10;

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

Reference£º
Article; Londregan, Allyn T.; Piotrowski, David W.; Futatsugi, Kentaro; Warmus, Joseph S.; Boehm, Markus; Carpino, Philip A.; Chin, Janice E.; Janssen, Ann M.; Roush, Nicole S.; Buxton, Joanne; Hinchey, Terri; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1407 – 1411;,
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 4-chloropyrrolo[l,2-b]pyridazine-3-carbonitrile (15g) (0.15 g, 0.84 mmol) in DMF (2 mL) was added at room temperature tetrahydrofuran-3-amine (53a) (0.22 mgs, 2.52 mmol), DIPEA (0.87 mL, 5 mmol) and stirred at room temperature overnight. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (10 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 10 mL). The organic layers were combined washed with water (2 x 10 ml), brine (10 mL), dried, filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 12g, eluting with 0-100% ethyl acetate in hexanes) to furnish 4-(tetrahydrofuran-3- ylamino)pyrrolo[l,2-b]pyridazine-3-carbonitrile (53b) (0.175 g, 91%) as a tan solid; 1H NMR (300 MHz, DMSO) d 7.95 (s, IH), 7.89 (d, J = 7.0, IH), 7.71 (dd, J = 1.6, 2.6, IH), 7.24 (dd, J = 1.6, 4.5, IH), 6.69 (dd, J = 2.7, 4.4, IH), 4.86 (dt, J = 3.6, 11.1, IH), 4.01 – 3.83 (m, 3H), 3.76 (td, J = 5.8, 8.3, IH), 2.39 – 2.23 (m, IH), 2.15 (m, IH); IR (KBr) 2194 cm-1; MS (ES-) 227.0(M-I) 262.9 (M+Cl); Analysis: Calcd for C12H12N4O? 0.25 H2O: C, 61.92; H, 5.41; N, 24.07; Found: C, 62.05; H, 5.23; N, 24.01., 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; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KOTIAN, Pravin L.; KUMAR, V. Satish; WU, Minwan; LIN, Tsu-Hsing; WO2011/14817; (2011); 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, The synthesis was conducted in flow. Reagent solution A contained 4-(4-chlorophenyl)isoquinoline-6-carboxylic acid (8 mg, 28.2 11mol), 0-(benzotriazol-1-yl)- N,N,N’,N’-tetramethyluronium tetrafluoroborate (TBTU, 10.9 mg, 33.8 11mol) and N,N diisopropylethylamine (10.9 mg, 14.8 111, 84.6 11mol) in dimethylformamide (230 Ill) and reagent solution B contained tetrahydrofuran-3-ylamine (106 111 of a 0.4 M stock solution in dimethylformamide, 42.3 11mol) in dimethylformamide (144 Ill). The two reagent solutions were injected (0.250 mL of each solution) by means of Gilson LH 215 auto-sampler into the reactor sample loops (Gilson 819). Then, both reagent streams were combined at aT-piece connectorand the reagent mixture heated at 120 ¡ãC for 5 min in a 10 ml PFA tube reactor coil. The crude product stream was purified in-line by preparative HPLC (C18 reverse phase, acetonitrile I water (0.05 percenttriethylamine)= 2:98 to 98:2) to yield the title compound as a colorless oil (2.2 mg,16 percent). MS: m/e = 353.4 [M+Ht.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECCARELLI, Simona M.; JAGASIA, Ravi; JAKOB-ROETNE, Roland; MARTIN, Rainer E.; WICHMANN, Juergen; WO2014/177596; (2014); 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.

Example 4: 8-Chloro-7-methoxy-W-(tetrahydrofuran-3-yl)quinazolin-4-amine: To a solution of 4,8-dichloro-7-methoxyquinazoline (650 mg, 2.84 mmol) in dimethylformamide (20 mL) was added tetrahydrofuran-3-amine (297 mg, 3.41 mmol) and diisopropylethylannine (0.99 mL, 5.7 mmol). Through the mixture was bubbled N2 for 5 minutes. The reaction was then heated at 100¡ãC for 3 hrs under an atmosphere of N2. The crude mixture was concentrated and the residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate and petroleum ether to give 8-chloro-7-methoxy-/V-(tetrahydrofuran-3-yl)quinazolin-4-amine 650 mg (82percent)., 88675-24-5

Big data 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; WO2015/150254; (2015); 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

To a solution of 2,4-dichloro-5-nitropyridine (386 mg, 2.0 mmol), and triethylamine (417 L, 3.0 mmol) in THF (6 mL) was added dropwise tetrahydrofuran-3-ylamine (208 mg, 2.4 mmol) and the reaction mixture was stirred for 1 h. An additional amount of tetrahydrofuran-3-ylamine (50 mg) was added and the reaction mixture was stirred for 1 h. The volatiles were removed in vacuo and the resulting residue was partitioned between water and EtOAc. The organic phase was dried (MgS04) and concentrated in vacuo to afford the title compound as a yellow solid (490 mg, quantitative). LCMS (ESI): [M+H]+ 244.2., 88675-24-5

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

Reference£º
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); 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 solution of N, N-diisopropylethylamine (3.20 mL, 18.4mmol), l-fluoro-2-nitrobenzene (0.484 mL, 4.59 mmol), and (+)-tetrahydrofuran-3 -amine (400 nig, 4.59 mmol) in 7z-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.; WO2006/31610; (2006); A2;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem