Tag: 111769-27-8

111769-27-8, (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 244 : (R)- l-(5,6-dichloro- 1-p-tolyl- lH-benzo [d] imidazol-2-yl)-7V-(tetrahydrofuran- 3-yl)piperidine-4-carboxamideEthyl l-(5,6-dichloro-lH-benzo[d]imidazol-2-yl)piperidine-4-carboxylate (110 mg, 0.321 mmol) dimethylsulfoxide (1 mL), caesium carbonate (147 mg, 0.45 mmol), l-iodo-4-methylbenzene (140 mg, 0.643 mmol), 8-hydroxyquinoline (9.3 mg, 0.064 mmol), polyethylene glycol 400 (64.3 mg, 0.161 mmol) and copper(I) oxide (4.6 mg, 0.032 mmol) was subjected to microwave conditions for one hour at 15O0C. The reaction mixture was diluted with N,N-dimethyl- formamide (4 mL), filtered and the filtrate concentrated in vacuo. The residue was dissolved in ethanol (4 mL) and aqueous sodium hydroxide (2 mL, 1 N), and stirred at room temperature over the weekend. The reaction mixture was treated with aqueous hydrochloric acid (1 mL, 2 N) and concentrated. The residue was mixed with N,N-dimethylformamide (13 mL), N,7V-diisopropyl- ethylamine (Hunig’s base, DIEA, 19.2 mg, 0.148 mmol), 2-(7-aza-lH-benzotriazole-l-yl)-1,1,3,3-tetramethyluronium hexafluoro-phosphate (EtaATU, 14.1 mg, 0.037 mmol) and (R)-(+)- tetrahydrofuran-3 -amine 4-methylbenzenesulfonate (9.6 mg, 0.0371 mmol). The reaction mixture was stirred at room temperature for 2 hours, concentrated in vacuo and purified on hplc (preparative RP-LC was performed on a Gilson system equipped with a Zorbax SB-C8 (5 mum, 21.2 x 150 mm) column, using methano I/water (0.05% formic acid) gradients at a flow rate of 4 niL/min with UV (214 or 254 nm) and MS (ESI) detection) to give 7.7 mg of (R)- 1 -(5,6- dichloro- 1 -p-tolyl- lH-benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4- carboxamide. LC-MS (m/z) 473.1 (M+ 1).

The synthetic route of 111769-27-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; STENBERG, Patric; WESTMAN, Jacob; WALLBERG, Hans; WO2011/23812; (2011); 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.111769-27-8,(R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

A mixture of (R)-l-(5,6-dichloro-lH-benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)- piperidine-4-carboxamide (100 mg, 0.261 mmol) dimethylsulfoxide (2 mL), caesium carbonate (0.392 mmol), 2-iodopyridine (0.783 mmol), 8-hydroxyquinoline (0.104 mmol), polyethylene glycol (0.511 mmol) and copper(I) oxide (0.0522 mmol) was subjected to microwave conditions for two hour at 120C. The reaction mixture was filtered and subjected to preparative hplc(performed on a Gilson-Finnigan ThermoQuest AQA system equipped with a Zorbax SB-C8 (5 muetaiota, 21.2 x 150 mm) column, using methanol/water (0.05 % formic acid) gradients at a flow rate of 15 mL/min with UV (214 or 254 nm) and MS (ESI) detection) to give 30 mg (25 % yield) of (R)- 1 -(5,6-dichloro- 1 -(pyridin-2-yl)- lH-benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3 – yl)piperidine-4-carboxamide as a pale yellow solid. LC-MS (m/z) 460.3 (M+l).

111769-27-8 (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate 14243169, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; WO2012/117062; (2012); 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.111769-27-8,(R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

c) Preparation of the intermediate compound (R)-l-(5,6-dichloro-lH-benzo[d]imidazol-2-yl)-N- (tetrahydrofuran-3-yl)piperidine-4-carboxamide l-(5,6-Dichloro-lH-benzo[d]imidazol-2-yl)piperidine-4-carboxylic acid (628 mg, 2.0 mmol), (R)-(+)-tetrahydrofuran-3-amine 4-methylbenzenesulfonate (622 mg, 2.4 mmol), 2-(7-aza-lH- benzotriazole-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (HATU, 912 mg, 2.4 mmol), JV,JV-diisopropylethylamine (Hunig’s base, DIEA, 775 mg, 6.0 mmol) and N5N- dimethylformamide (25 niL) was stirred at room temperature for 100 minutes. The reaction mixure was concentrated in vacuo, the residue purified on column (silica gel, flashchromatography, dichloromethane/methanol, gradient elution 4-20 % methanol) and finally precipitated from chloroform to give 378 mg (49 % yield) of (R)-l-(5,6-dichloro-lH- benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4-carboxamide as a white solid. LC- MS (m/z) 382.9 (M+ 1).

111769-27-8 (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate 14243169, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; STENBERG, Patric; WESTMAN, Jacob; WALLBERG, Hans; WO2011/23812; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

111769-27-8, (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Procedure S3: To a solution of 3-[(4-fluoro-3-methyl-phenyl)carbamoyl]benzene- sulfonyl chloride (0.50 g, 1.52 mmol, 1 eq) and DIPEA (657 mu, 3.81 mmol, 2.5 eq) in CH2CI2 (10 mL), an amine (1.1 eq) was added. The reaction mixture was stirred for 1 hour. Next, 1M HC1 (5 mL) was added to the reaction mixture. Workup W2: The organic layer was separated and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using a heptane to EtOAc gradient as eluent. Compound 129 Synthesis following procedure S3 with R-(+)-3-aminotetrahydrofuran toluene-4- sulfonate as amine, workup W2. Method F; Rt: 0.89 min. m/z: 396.1 (M+NH4)+ Exact mass: 378.1. 1 H NMR (400 MHz, DMSO-dg ) ppm 1.56 – 1.65 (m, 1 H), 1.85 – 1.94 (m, 1 H), 2.25 (d, J=1.8 Hz, 3 H), 3.36 (dd, J=9.0, 4.4 Hz, 1 H), 3.52 – 3.65 (m, 2 H), 3.65 – 3.73 (m, 1 H), 3.73 – 3.79 (m, 1 H), 7.14 (t, J=9.2 Hz, 1 H), 7.56 – 7.62 (m, 1 H), 7.67 (dd, J=7.0, 2.3 Hz, 1 H), 7.78 (t, J=7.8 Hz, 1 H), 7.99 – 8.05 (m, 1 H), 8.08 (bs, 1 H), 8.20-8.23(m, 1 H), 8.37 (t, J=1.7 Hz, 1 H), 10.47 (s, 1 H), []D = + 5.8 (c 0.61 w/v %, MeOH)

As the paragraph descriping shows that 111769-27-8 is playing an increasingly important role.

Reference£º
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (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.111769-27-8,(R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

A 0 C. suspension of (R)-(+)-tetrahydro-3-furylamine p-toluenesulfonate salt (1.00 g, 3.86 mmol) in THF (40 mL) was treated with NaH (60% in mineral oil, 0.170 g, 4.24 mmol), stirred at 0 C. for 1.5 h, treated with 2-chloroethyl isocyanate (0.362 mL, 4.24 mmol) and stirred at RT overnight as the cooling bath expired. The mixture was treated with satd. NH4Cl and water, extracted with EtOAc (2*) and the combined organics were washed with brine (2*), dried over Na2SO4 and concentrated to dryness. The residue was treated with 1:1 EtOAc/Hex and the resulting solid collected via filtration to afford (R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (522 mg, 70%). MS (ESI) m/z: 193.1 (M+H+).

As the paragraph descriping shows that 111769-27-8 is playing an increasingly important role.

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem