Category: 33420-52-9

Electric Literature of 33420-52-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 33420-52-9, name is 2,2-Difluoropropan-1-ol. A new synthetic method of this compound is introduced below.

General procedure: A mixture of 5-chloro-3-[(2-chlorophenyl)methyl]-7-(3,3-difluoropyrrolidin-l- yl)triazolo[4,5-d]pyrimidine (example 8, step a) (38.5 mg, 0.1 mmol), 2,2,2-Trifluoro- ethanol (99 mg, 1 mmol) and NaH (suspension in oil, 20 mg, 5 mmol) in DMF (1 mL) was stirred at 110 C for 6 h. After cooling to room temperature formic acid was added and the mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. After evaporation of the product containing fractions 29.3 mg (65 %) of the title compound was isolated. MS(m/e): 449.2 (MH+). Example 53; 3-[(2-Chlorophenyl)methyl]-5-(2,2-difluoropropoxy)-7-(3,3-difluoropyrrolidin-l- yl)triazolo[4,5-d]pyrimidine; In analogy to the procedure described for the synthesis of 3-[(2-chlorophenyl)methyl]-7- (3,3-difluoropyrrolidin-l-yl)-5-(2,2,2-trifluoroethoxy)triazolo[4,5-d]pyrimidine (example 40) the title compound was prepared from 5-chloro-3-[(2-chlorophenyl)methyl]-7-(3,3- difluoropyrrolidin-l-yl)triazolo[4,5-d]pyrimidine and 2,2-difluoropropan-l-ol with the use of Cs2C03 instead of NaH. MS(m/e): 445.3 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
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Reference of 33420-52-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

7-[ 1 -(tert-butoxycarbonyl)piperidin-4-yl] -2-methyl-5-oxo-4,5-dihydropyrazolo[ 1 ,5-a]pyrimidine-3- carboxylic acid (100 mg, 266 muiotaetaomicron) was dissolved in tetrahydrofurane (5.0 ml, 62 mmol) and Nu,Nu’- Carbonyldiimidazole (86.2 mg, 531 muiotaetaomicron) was added. The mixture was heated at reflux for 1.5 h. Solvents were removed and 2,2-difluoropropan-l-ol (3.01 g, 31.4 mmol) was added. The mixture was heated at reflux for 18h and then purified by preparative HPLC (Method: column: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / solvents: A = water (0,01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10%B, 6.50min = 20%B, 17.0-19.75min = 100%B, 19.75.00-23.00min = 90%B). Evaporation of the combined product fractions yielded the title compound (105 mg, 99 % purity, 86 % of theory). LC-MS (Method 1 IB): Rt = 2.03 min; MS (ESIneg): m/z = 453 [M-H]

According to the analysis of related databases, 33420-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
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Synthetic Route of 33420-52-9, Adding some certain compound to certain chemical reactions, such as: 33420-52-9, name is 2,2-Difluoropropan-1-ol,molecular formula is C3H6F2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33420-52-9.

Example 2305- [9-(2,2-Difluoropropoxy)-6-methanesulfonyl-5- [(S)-oxan-4-yl(phenyl)methylj -5H-pyrido [3 ,2-bj indol-3-ylj -4-(2H3)methyl- 1-methyl- 1H-1 ,2,3-triazole To a stirred solution of 5- {9-fluoro-6-methanesulfonyl-5 – [(S)-oxan-4-yl(phenyl)methyl] -5H-pyrido [3 ,2-b]indol-3 -yl} -4-(2H3)methyl- 1-methyl-i H- 1,2,3 -triazole (31.0 mg, 0.0600 mmol) and 2,2-difluoropropan-2-ol (27.8 mg, 0.290 mmol) inNMP (0.30 mL) was added t-BuOK (25.9 mg, 0.230 mmol). This mixture was heated at65 C for 1 h and cooled to room temperature. The mixture was diluted with MeOH andpurified via preparative LC/MS with the following conditions: Column: Waters XBridgePhenyl, 19 x 200 mm, 5-rim particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mMammonium acetate; Gradient: 15-70% B over 20 mm, then a 5-mm hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 5- [9-(2,2-difluoropropoxy)-6-methanesulfonyl-5 – oxan-4-yl(phenyl)methyl]-5H-pyrido [3 ,2-b]indol-3 -yl]-4-(2H3)methyl- i-methyl-i H15 1,2,3-triazole (13.8 mg, 37%). ?H NMR (500MHz, DMSO-d6) oe 8.60 (s, 1H), 8.29 (d,J8.8 Hz, 1H), 7.74 (s, 1H), 7.56 (br d, J7.7 Hz, 2H), 7.36-7.29 (m, 2H), 7.28-7.22 (m,1H), 7.18 (d, J=8.9 Hz, 1H), 6.74 (s, 1H), 4.67 (br t, J=12.0 Hz, 2H), 3.86 (br d, J15.iHz, 1H), 3.73 (s, 3H), 3.60-3.55 (m, 1H), 3.49 (brt,J=ii.5 Hz, 1H), 3.33 (br d,J11.8Hz, 1H), 3.23-3.16 (m, 1H), 2.54 (s, 3H), 1.95 (brt,J=19.4 Hz, 3H), 1.69 (br d,J10.8Hz, 1H), i.62-i.50(m, 1H), i.22(brd,J=8.8 Hz, 1H), 0.43 (brd,J=12.OHz, 1H).LCMS: RT = 1.731 mm; (ES): mlz (M+H)+ = 613.15, LCMS: Column: Waters Acquity UPLC BEH C 18, 2.1 x 50 mm, 1 .7-tim particles; Mobile Phase A: 5:95 acetonitrile:water with 10mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10mM ammonium acetate; Temperature: 50 C; Gradient: 0-100% B over 3 mm, then a 0.75-mmhold at 100% B; Flow: 1.11 mL/min. HPLC Purity at 220 nm: 95 %.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 33420-52-9, 2,2-Difluoropropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 33420-52-9, Adding some certain compound to certain chemical reactions, such as: 33420-52-9, name is 2,2-Difluoropropan-1-ol,molecular formula is C3H6F2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33420-52-9.

To a cooled (0 C) solution of 2,2-difluoropropan-l-ol (3.17 g, 33.0 mmol) and pyridine (2.97 mL, 36.7 mmol) in CH3CN (100 mL) was added dropwise Tf20 (5.70 mL, 33.8 mmol). The reaction was stirred for 30 min at 0 C. To the cooled slurry was added a cold solution of methyl 4-methyl-5-(l-(piperidin-4-yl)propyl)thiophene-3 -carboxylate hydrochloride (2.6 g, 7.34 mmol) and K2C03 (9.13 g, 66.0 mmol) in CH3CN (20 mL). The reaction was allowed to warm to RT, then heated at 50 C overnight. The reaction was evaporated to dryness under vacuum, taken up in DCM, washed with water, brine, dried (Na2S04), filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (Isco RediSep Rf Gold 120 g, 5% EtOAc:hexanes) to give methyl 5-(1- (1-(2,2-difluoropropyl)piperidin-4-yl)propyl)-4-methylthiophene-3-carboxylate (2.05 g, 5.42 mmol, 73.8 % yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.00 (s, 1H), 3.85 (s, 3H), 2.99 (d, J=11.12 Hz, 1H), 2.86 (d, J=11.12 Hz, 1H), 2.53-2.75 (m, 3H), 2.37 (s, 3H), 2.04-2.27 (m, 2H), 1.84-2.01 (m, 2H), 1.62 (t, J=18.69 Hz, 4H), 1.30-1.47 (m, 5H), 0.76 (t, J=7.33 Hz, 3H). MS(ES) [M+H]+ 360.2.

According to the analysis of related databases, 33420-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (112 pag.)WO2016/66697; (2016); A1;,
Alcohol – Wikipedia,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, molecular weight is 96.076, as common compound, the synthetic route is as follows.Recommanded Product: 33420-52-9

Step 4 (ME-54):A solution of crude ME-53 (3.8 g, 39.58 mmol) in Dimethyl formamide (5 mL) was added to asuspension of sodium hydride (60%; 1 .3 g, 32.5 mmol) in dry dimethyl formamide (20 mL) at 0C and the mixture was stirred at room temperature for 1 h. The reaction mass was again cooled to 0C and a solution of 5-bromo-2-fluoro benzonitrile (2.36 g, 11.8 mmol) in dimethyl formamide (5 mL) was added. The reaction mass was warmed to room temperature and stirred for 30 mm, quenched with saturated ammonium chloride solution and extracted withdiethyl ether. The combined organic layer was washed successively with water, brine; dried over anhydrous sodium sulfate and concentrated in vacuum to afford the crude intermediate. Purification by column chromatography over silica gel (60-l20mesh) and using 8% ethyl acetate in pet ether as the eluent afforded 2.5 g (69.4%) of ME-S4 as a yellow gummy liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33420-52-9, 2,2-Difluoropropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; PROBIODRUG AG; HEISER, Ulrich; BUCHHOLZ, Mirko; SOMMER, Robert; DEMUTH, Hans-Ulrich; WO2014/140279; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Product Details of 33420-52-9

To a solution of 2,2-difluoropropan-1-ol (1.30 g) in THF (25 mL) was added 60% sodium hydride (0.64 g) at0C, and the mixture was stirred at the same temperature for 20 min. To the reaction mixture was added methyl 4,6-dichloropyrimidine-5-carboxylate (2.55 g), and the mixture was stirred under an argon atmosphere at 0C for 1 hr. Thereaction mixture was diluted with ethyl acetate, and the organic layer was washed with saturated brine, and dried overanhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (ethyl acetate/hexane) to give the title compound (2.81 g).1H NMR (300 MHz, DMSO-d6) delta 1.70 (3H, t, J = 19.2 Hz), 3.92 (3H, s), 4.77 (2H, t, J = 12.8 Hz), 8.84 (1H, s).

With the rapid development of chemical substances, we look forward to future research findings about 33420-52-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; SHIMOKAWA, Kenichiro; KOJIMA, Takuto; SAKAMOTO, Hiroki; FUJIMORI, Ikuo; NAKAMURA, Minoru; YAMADA, Masami; MURAKAMI, Masataka; KAMATA, Makoto; SUZUKI, Shinkichi; (78 pag.)EP3144308; (2017); A1;,
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Synthetic Route of 33420-52-9 ,Some common heterocyclic compound, 33420-52-9, molecular formula is C3H6F2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To tert-butyl 4-(1-(4-(methoxycarbonyl)-3-methylthiophen-2-yl)propylidene)piperidine-1-carboxylate (12.1 g, 31.9 mmol) was added HC1 in dioxane (30 mL, 120 mmol). After stirring for 30 min the reaction was evaporated to dryness to give the crude amine hydrochloride salt as a white solid foam. To a stirred solution of 2,2-difluoropropan-l-ol (16.3 g, 170 mmol) and pyridine (16.3 mL, 202 mmol) in CH3CN (250 mL) at 0 C in an ice bath was added dropwise Tf20 (28 mL, 166 mmol). The reaction was stirred for 30 min at 0 C, then added cold to a slurry of the above amine hydrochloride and K2C03 (46.8 g, 339 mmol) in CH3CN (100 mL). The reaction was rinsed down with CH3CN (50 mL). The reaction was allowed to warm to RT, heated to 50 C and stirred for 6 h. The reaction was evaporated to dryness under vacuum, taken up in DCM, washed with water, brine, dried (Na2S04), filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (Isco RediSep Rf Gold 120g, 5 to 15% EtOAc in hexanes). The pure fractions were combined and evaporated to dryness under vacuum to give methyl 5-(1-(1-(2,2- difluoropropyl)piperidin-4-ylidene)propyl)-4-methylthiophene-3 -carboxylate ( 10.05 g, 24.74 mmol, 78 % yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 8.03 (s, 1H), 3.86 (s, 3H), 2.70 (t, J=12.6 Hz, 4H), 2.57 – 2.43 (m, 4H), 2.32 (br. s., 2H), 2.25 (s, 3H), 2.06 (br. s., 2H), 1.67 (t, J=18.8 Hz, 3H), 0.94 (t, J=7.5 Hz, 3H). MS(ES) [M+H]+ 358.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (112 pag.)WO2016/66697; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 33420-52-9, Adding some certain compound to certain chemical reactions, such as: 33420-52-9, name is 2,2-Difluoropropan-1-ol,molecular formula is C3H6F2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33420-52-9.

To a solution of 2,2-difluoropropan-1-ol (5.00 g, 52.0 mmol) and triethylamine (9.40mL, 67.6 mmol) in DCM (75 mL) was added trifluoromethanesulfonic anhydride (10.5 mL, 62.4mmol) dropwise at -20 C, and then allowed to move to 0 C, stirred overnight. The mixture wasdiluted with DCM (75 mL), then poured into ice water (100 mL). The separated organic layerwas washed with 20% Na2C03 aqueous solution (50 mL) and brine (50 mL) successively, anddried over Na2S04, filtered and concentrated in vacuo to afford the target compound as black oil(11.41 g, yield 96.1%).1HNMR (400 MHz, DMSO-d6) 8 (ppm): 5.08 (t, J= 13.5 Hz, 2H), 1.72 (t, J= 19.3 Hz, 3H);19F NMR (376 MHz, DMSO-d6) 8 (ppm): -74.6, -99.7.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 33420-52-9, 2,2-Difluoropropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; DAI, Weilong; XI, Ning; LI, Minxiong; ZHANG, Tao; LI, Xiaobo; HU, Haiyang; CHEN, Wuhong; WANG, Tingjin; LIU, Jun; (188 pag.)WO2017/48675; (2017); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 33420-52-9, 2,2-Difluoropropan-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 33420-52-9, blongs to alcohols-buliding-blocks compound. SDS of cas: 33420-52-9

To a solution of 2,2-difluoropropan-1-ol (I-10A-7b; 1.76 g, 18.3 mmol), dimethylaminopropylamine (DMAP: 157 mg, 1.3 mmol), and triethylamine (2.20 g, 3.1 ml, 22 mmol) in CH2Cl2 (15 ml) at 0 C. was added triflic anhydride (Tf2O; 6.2 g, 3.7 ml, 22 mmol). The reaction mixture initially turned a pink color, then a yellow color following the complete addition of Tf2O. The reaction mixture was stirred at 0 C. for 2 hours and diluted with CH2Cl2. The organic solution was washed with water, 1 M aqueous citric acid, and saturated aqueous NaHCO3, dried, and concentrated under reduced pressure (225 mm/Hg; bath temperature -30 C.) to give the desired product, trifluoromethanesulfonic acid 2,2-difluoropropyl ester (I-10A-7c), as a pink oil (3 g, 72%): 1H NMR (400 MHz, CDCl3) delta 4.49 (t, J=10.8 Hz, 2H), 1.74 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; Pfizer Inc.; US2004/214837; (2004); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 33420-52-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation of Intermediate Trifluoromethanesulfonic acid 2,2-difluoropropyl ester (I-4A-4c): To a solution of 2,2-difluoro-propan-1-ol (I-4A-4b, 1.76 g, 18.3 mmol), DMAP (157 mg, 1.3 mmol), and NEt3 (2.20 g, 3.1 ml, 22 mmol) in CH2Cl2 (15 ml) at 0 C. was added trifluoromethanesulfonic anhydride (Tf2O, 6.20 g, 3.7 ml, 22 mmol). The reaction mixture initially turned a pink color, then a yellow color following the complete addition of Tf2O. The reaction mixture was stirred at 0 C. for 2 h and diluted with CH2Cl2. The organic solution was washed with H2O, 1 M citric acid, and saturated aqueous NaHCO3, dried, and concentrated under reduced pressure (225 mm/Hg; water bath temperature -30 C.) to give the desired product, trifluoromethanesulfonic acid 2,2-difluoro-propyl ester (I-4A-4c), as a pink oil (3 g, 72%): 1H NMR (400 MHz, CDCl3): delta 4.49 (t, 2H, J=10.8 Hz), 1.74 (t, 3H).

According to the analysis of related databases, 33420-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2004/214838; (2004); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts