Category: 97-99-4

97-99-4,97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: NaH (38.5 mg, 0.96 mmol (60% in mineral oil)) was added to a 50 ml round-bottom flask and dry DMF was added.(DMF will not dissolve NaH but it will be a suspension). To this mixture was added 2-fluoroethanol (18.50 mg, 0.29 mmol) at room temperature, and the mixture wasstirred for 10 min.To the suspension was added 2-(3-(5-fluoropyridin-3-yl)phenyl)imidazo[1,2-a]pyridine-8-carboxamide (80 mg, 0.24 mmol), and the resulting mixture was heated at 100C for 2 hr.The DMF was evaporated, and the crude material was purified by silica gel column chromatography eluting with 0-20% MeOH/DCM. The material thus produced was further purified by Gilson Prep HPLC to obtain desired product 2-(3-(5-(2-fluoroethoxy)pyridin-3-yl)phenyl)imidazo[1,2-a]pyridine-8-carboxamide (15.00 mg, 16.56 %).

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ramachandran, Sreekanth; Panda, Manoranjan; Mukherjee, Kakoli; Choudhury, Nilanjana Roy; Tantry, Subramanyam J.; Kedari, Chaitanya Kumar; Ramachandran, Vasanthi; Sharma, Sreevalli; Ramya; Guptha, Supreeth; Sambandamurthy, Vasan K.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 17; (2013); p. 4996 – 5001;,
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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

97-99-4, Example 11; N-[(3E)-5-tert-butyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]isoxazol-3(2H)-ylidene]-5-chloro-2-methoxybenzamide; Example 11A; (2R)-tetrahydrofuran-2-ylmethyl 4-methylbenzenesulfonate; To (R)-(tetrahydrofuran-2-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (3 mL) and pyridine (3 mL) at ambient temperature was added 4-methylbenzene-1-sulfonyl chloride (2.0 g, 10.3 mmol) portion-wise over 5 minutes. This mixture was stirred for 16 hours at ambient temperature then was quenched with 10 mL of 5% aqueous HCl and was extracted with 3¡Á5 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 75% hexanes in ethyl acetate) to give the title compound (1.7 g, 6.8 mmol, 69% yield). MS (DCI/NH3) m/z 257 (M+H)+ and 274 (M+NH4)+.

As the paragraph descriping shows that 97-99-4 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/249129; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,97-99-4

To a solution of (2R)-tetrahydrofuran-2-ylmethanol (58 mg, 0.57 mmol) in dry DMF (5 mL) was added NaH (23 mg, 60% in mineral oil, 0.57 mmol) under a N2 atmosphere. After the addition, the reaction mixture was stirred at room temperature for 1 hr. Then, to the mixture was added (2R)-2-[({2-chloro-6-[4-(1 /-/-pyrazolo[3,4-b]pyridin-3-yl)piperidin-1 -yl]pyrimidin-4- yl}carbonyl)amino]propyl benzoate (1-183) (100 mg, 0.19 mmol). After the addition, the resulting mixture was heated at 50 C for 4 hr. LCMS showed the reaction was completed. The mixture was cooled to room temperature and quenched with H20 (20 mL). The mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (4 x 50 mL), dried over Na2S04 and concentrated to give the residue, which was purified by silica gel chromatography (CH2CI2/MeOH = 10/1 , Rf ~ 0.6) to give the crude product, which was further purified with preparative HPLC(Column: Phenomenex Gemini C18 250 x 21 .2 mm, deltamuetaiota. Mobile phase: from 20% MeCN (0.225% HCOOH) in water to 40% MeCN (0.225% HCOOH) in water. Wavelength: 220 nm) Lyophilization afforded N-[(2f?)-1 -hydroxypropan-2-yl]-6-[4-(1 H- pyrazolo[3,4-b]pyridin-3-yl)piperidin-1 -yl]-2-[(2R)-tetrahydrofuran-2-ylmethoxy]pyrimidine-4- carboxamide (Example 80) (20.1 mg, 22%) as a white solid. LCMS (APCI), m/z 482.2 [M + H]+; (400 MHz, DMSO-c/s) 8 ppm 13.29 (br. s., 1 H), 8.48 – 8.49 (m, 1 H), 8.31 (d, J = 8.0 Hz, 1 H), 8.18 (d, J = 8.8 Hz, 1 H), 7.13 -7.16 (m, 1 H), 7.04 (s, 1 H), 4.89 (t, J = 5.5 Hz, 1 H), 4.50 (br. s., 1 H), 4.26 (d, J = 5.5 Hz, 2 H), 4.12 – 4.18 (m, 1 H), 4.03 – 4.04 (m, 1 H), 3.77 – 3.82 (m, 1 H), 3.65 -3.70 (m, 1 H), 3.42 – 3.47 (m, 3 H), 3.16 – 3.23 (m, 2 H), 3.00 (br. s., 1 H), 2.12 (d, J = 1 1 Hz, 2 H), 1.96 – 2.04 (m, 1 H), 1 .81 -1 .88 (m, 4 H), 1 .62 – 1 .71 (m, 1 H), 1 .15 (d, J = 6.5 Hz, 3 H).

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

97-99-4, Example 22CN-[(2Z)-5-tert-butyl-3-[2R)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-ylidene]-2-[(2R)-tetrahydrofuran-2-ylmethoxy]-5-(trifluoromethyl)benzamideIn a 50 mL round-bottomed flask, (R)-(tetrahydrofuran-2-yl)methanol (176 mg, 1.74 mmol) was dissolved in tetrahydrofuran (8 ml). Sodium t-butoxide (176 mg, 1.83 mmol) was added and stirred at room temperature for 20 min before Example 22B (375 mg, 0.87 mmol) in tetrahydrofuran (5 mL) was added and stirred for 2 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate (3¡Á20 ml). The organics were combined, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by Analogix Intelliflash280 (SiO2, 0-30% hexanes in ethyl acetate) to afford the title compound (210 mg, 47% yield). 1H NMR (300 MHz, DMSO-d6) delta ppm 1.32 (s, 9H) 1.59-1.68 (m, 1H) 1.75-2.00 (m, 7H) 3.60-3.69 (m, 2H) 3.70-3.82 (m, 2H) 4.04-4.10 (m, 2H) 4.11-4.24 (m, 3H) 4.25-4.32 (m, 1H) 7.25 (s, 1H) 7.28 (d, J=8.82 Hz, 1H) 7.73 (dd, J=8.65, 1.87 Hz, 1H) 7.94 (d, J=2.37 Hz, 1H); MS (DCI/NH3) m/z 513 (M+H)+. Anal. calcd C25H31F3N2O4S: C, 58.58; H, 6.1; N, 5.47. Found: C, 58.34; H, 6.22; N, 5.28.

97-99-4 (Tetrahydrofuran-2-yl)methanol 7360, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/63022; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,97-99-4

Example 10A (R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)methyl)hydrazine-1,2-dicarboxylate To a mixture of (R)-(tetrahydrofuran-2-yl)methanol (Fluka, 4.0 g, 39.2 mmol) and di-tert-butyl hydrazine-1,2-dicarboxylate (9.1 g, 39.2 mmol) in THF (50 mL) was added triphenylphosphine (14.4 g, 54.8 mmol) followed by (E)-di-tert-butyl diazene-1,2-dicarboxylate (12.6 g, 54.8 mmol), portionwise. This mixture was stirred at ambient temperature for 16 h then was concentrated under reduced pressure and purified by column chromatography (SiO2, 99% hex/EtOAc to 25% hex/EtOAc) to give the title compound (11.8 g, 37.3 mmol, 95% yield). MS (DCI/NH3) m/z 317 (M+H)+.

As the paragraph descriping shows that 97-99-4 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/41720; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

97-99-4,97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the product of Example 1E (0.10 g, 0.23 mmol) in THF (5 mL) was added potassium tert-butoxide (0.053 g, 0.47 mmol). The mixture was stirred at ambient temperature for 20 min then (R)-(tetrahydrofuran-2-yl)methanol (Fluka, 0.023 mL, 0.23 mmol) in THF (5 mL) was added via cannula. The mixture was stirred for 1 h at ambient temperature then was quenched with saturated, aqueous NH4Cl (3 mL) and diluted with EtOAc (3 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3¡Á5 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 50% hexanes in EtOAc to 100% EtOAc to 10% MeOH in EtOAc) to give the title compound (40 mg, 0.078 mmol, 34% yield). 1H NMR (300 MHz, CDCl3) delta ppm 1.43 (s, 9H), 1.68-1.81 (m, 2H), 1.82-1.96 (m, 4H), 1.97-2.11 (m, 2H), 3.66-3.80 (m, 3H), 3.85 (s, 3H), 3.86-3.93 (m, 1H), 3.99-4.06 (m, 1H), 4.10-4.22 (m, 2H), 4.25-4.36 (m, 2H), 4.46-4.54 (m, 1H), 6.99-7.04 (m, 1H), 7.00 (s, 1H), 7.44-7.51 (m, 1H), 7.96 (d, J=2.4 Hz, 1H); MS (DCI/NH3) m/z 510 (M+H)+

As the paragraph descriping shows that 97-99-4 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/69348; (2010); 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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

Example 193 : (R)-N-( 1 -Methyl- 1 H-pyrazo 1-4-yl)- 1 -((6-((tetrahydrofuran-2- yl)methoxy)pyridin-2-yl)methyl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine(R)-(Tetrahydrofuran-2-yl)methanol (22mg, 0.214mmol) was added to a solution of NaH (lOmg, 0.246mmol) in dry DMF (ImL) in a 2-necked flask under Nitrogen. Another portion of NaH (lOmg, 0.246mmol) was added to a stirring solution of l-((6-fluoropyridin-2- yl)methyl)-N-( 1 -methyl- 1 H-pyrazo 1-4-yl)- 1 H-pyrazolo [3 ,4-d]pyrimidin-6-amine (Example 170) (50mg, 0.154mmol) in DMF (1ml). This solution was added to the 2-necked flask and stirred for 16h at rt. The reaction was quenched with NH4C1 (sat. solution, ImL) and diluted with Ethyl Acetate (20mL). The organics were separated and washed with NaHC03 (sat. solution, 20mL). The aqueous phase was re-extracted with Ethyl Acetate (2 x lOmL). The combined organics were dried over Na2S04, filtered and the solvent evaporated to give a crude product that was purified by prep HPLC. (R)-N-( 1 -methyl- 1 H-pyrazo 1-4-yl)- 1 -((6- ((tetrahydrofuran-2-yl)methoxy)pyridin-2-yl)methyl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine was obtained as a white solid (24mg, 38% yield). 1H NMR (d6-Acetone) delta 8.87 (s, 1H), 8.04 (s, 1H), 7.99 (s, 1H), 7.61 (s and t, 2H), 6.70 (d, 1H), 6.64 (d, 1H), 5.54 (s, 2H), 4.07 (m, 3H), 3.82 (s, 3H), 3.75 (m, 1H), 3.61 (m, 1H), 1.84 (m, 3H), 1.54 (m, 1H); LC-MS method B, (ES+) 407.1, RT = 7.65min., 97-99-4

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

97-99-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

Example 80A (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate To a solution of (R)-tetrahydrofurfuryl alcohol (Lancaster, 1.0 g, 9.8 mmol) in 5 mL of CH2Cl2 and 5 mL of pyridine was added p-toluenesulfonyl chloride (2.8 g, 14.7 mmol) in portions over 15 minutes. The mixture was stirred at ambient temperature for 3 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 5 mL portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. MS (DCI/NH3) m/z 257 (M+H)+, 274 (M+NH4)+.

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; US2008/242654; (2008); 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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

97-99-4, j00431j To a solution of (R)-1-(tetrahydrofuran-2- yl)-methanol (0.50 g, 4.9 mmol), and DIPEA (2.56 mL, 14.7 mmol) in methylene chloride (20 mL) at 0 C was added methanesulfonyl chloride (398 jiL, 5.14 mmol). After 1 h at 0 C, the reaction was stirred at room temp over night (16 h) then quenched with H20 (20 mL), extracted with DCM (3 x 30 mL). The combined organic layers were washed with H20, dried (Na2504) and concentrated to give 551 mg (62%) of crude product. This material was used for next step without purification.

97-99-4 (Tetrahydrofuran-2-yl)methanol 7360, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; CEPHALON, INC.; BECKNELL, Nadine, C.; DANDU, Reddeppa, Reddy; DORSEY, Bruce, D.; GOTCHEV, Dimitar, B.; HUDKINS, Robert, L.; WEINBERG, Linda; ZIFICSAK, Craig, A.; ZULLI, Allison, L.; (411 pag.)WO2016/205633; (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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

97-99-4, Example 45; N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-5-chloro-2-methoxybenzamide; Example 45A; (R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride; To (R)-(tetrahydrofuran-2-yl)methanol (4.0 g, 39.2 mmol), di-tert-butyl hydrazine-1,2-dicarboxylate (3.64 g, 15.67 mmol) and triphenylphosphine (15.41 g, 58.7 mmol) in THF (100 mL) was added (E)-di-tert-butyl diazene-1,2-dicarboxylate (13.5 g, 5.87 mmol). The mixture was stirred at ambient temperature for 3 h then diluted with water and extracted with EtOAc (100 mL¡Á2). The organic extract was washed with brine and concentrated. Purification by flash chromatography (silica gel, 5-30% EtOAc/hexane) afforded 10.2 g (82%) of (R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)-methyl)-hydrazine-1,2-dicarboxylate, which was dissolved in a solution of 4M HCl in dioxane (40 mL) and stirred at ambient temperature overnight. The solvent was removed under reduced pressure and ethyl acetate (20 mL) was added with stirring. The solid precipitate was filtered, washed with ether (10 mL) and dried under vacuum to yield 7.8 g (97%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.48-1.63 (m, 1H), 1.73-1.88 (m, 2H), 1.90-2.02 (m, 1H), 2.84-3.01 (m, 2H), 3.61-3.71 (m, 1H), 3.72-3.83 (m, 1H), 3.97-4.08 (m, 1H), 5.76 (br, 5H); MS (ESI) m/z 117 (M+H)+.

As the paragraph descriping shows that 97-99-4 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/249129; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem