Category: 1009102-44-6

Reference of 1009102-44-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1009102-44-6 as follows.

To a soution of (E)-3-((3aS,5aR,5bR,7aR,9S, 11 aR, 11 bR, 13aS)-9-hydroxy-1 – isopropyl-5a,5b,8,8, 11 a-pentamethyl-2-oxo- 3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a, 11b, 12,13, 13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)acrylic acid (500 mg, 1.007 mmol), 1-(4- chlorophenyl)cyclopropanamine hydrochloride (226 mg, 1.107 mmol) and HATU (765 mg, 2.013 mmol) in Nu,Nu-dimethylformamide (DMF) (2 mL) stirred at 0C was added DIPEA (0.703 mL, 4.03 mmol) . The reaction mixture was stirred at 20 C for 1 h. The reaction mixture was adjusted pH to 3-4 by 2 M HCI, filtered, and the solid was washed with water (50 mL), solved into DCM, dried over sodium sulfate and evaporated in vacuo to give the crude product. The crude product was washed with petrol ether/EtOAc/DCM (10/1/1) to afford the target product (E)-N-(1-(4-chlorophenyl)cyclopropyl)-3- ((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a, 5b, 8,8,11 a- pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9, 10,11, 11a, 11b, 12, 13,13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)acrylamide (685 mg, 1.007 mmol, 100 %)) as a yellow soild.

According to the analysis of related databases, 1009102-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAN, Nianhe; JOHNS, Brian Alvin; TANG, Jun; WO2013/90683; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1009102-44-6, A common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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.

l-(4-chlorophenyl)cyclopropanamine hydrochloride (25 mg, 0.123 mmol) was added to a stirring solution of HATU (59 mg, 0.154 mmol), DIEA (54 mu, 0.308 mmol), and 3-(2-(4-fluorophenyl)-3- (methylcarbamoyl)benzofuran-5-yl)benzoic acid (40 mg, 0.103 mmol) in DMF (1 mL) at rt. It was allowed to stir for 1 hour. The mixture was diluted with EtOAc and washed with sat NaHC03, and sat NaCl. The organic phase was dried over Na2S04, filtered and concentrated and was purified by preparative reverse phase HPLC on a C18 column using a suitably buffered H20/CH3CN gradient, and concentrated to give the titled compound (8 mg, 14%). 1H NMR (500 MHz, DMSO-d6) d ppm 9.37 (1 H, s), 8.46 – 8.55 (1 H, m), 8.22 (1 H, s), 7.95 – 8.05 (2 H, m), 7.86 – 7.95 (3 H, m), 7.74 – 7.83 (2 H, m), 7.59 (1 H, t, J=7.63 Hz), 7.38 – 7.44 (2 H, m), 7.30 – 7.36 (2 H, m), 7.20 – 7.28 (2 H, m), 2.86 (3 H, d, J=4.58 Hz), 1.26 – 1.36 (4 H, m). LC-MS retention time: 1.92 min; m/z (MH+): 539. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna lOu CI 8 3.0x50mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220nM. The elution conditions employed a flow rate of 5 ml/min , a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% MeOH / 90% H20 / 0.1% trifluoroacetic acid and solvent B was 10% H20 / 90% MeOH / 0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A = 5% CH3CN/95%H2O/0.1% TFA, Solvent B = 95% CH3CN/5% H2O/0.1% TFA, Start %B = 10, Final %B = 100, Gradient time = 15 min, Stop time = 18 min, Flow Rate = 1 ml/min. Column: Waters Sunfire C-18, 4.6 x 150 mm, 3.5 mm, Rt = 14.56 min, purity = 99%; Column: Waters Xbridge Phenyl column 4.6 x 150 mm, 3.5 mm, Rt = 13.20 min, purity = 97%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; PARCELLA, Kyle, E.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine, A.; HAN, Ying; HEWAWASAM, Piyasena; KADOW, John, F.; NICKEL, Andrew; WO2011/112191; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1009102-44-6, These common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, 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.

In step 1 Manufactured 1-(4-chlorophenyl)cyclopropan-1-amine hydrochloride (0.500 g, 2.450 mmol), ethyl 2-chloropyrimidine-5-carboxylate (0.503 g, 2.695 mmol) and N,N-diisopropylethylamine (1.280 mL, 7.350 mmol) was dissolved in 1,4-dioxane (10 mL) at room temperature and stirred at 110 C for 18 hours, and then the temperature was lowered to room temperature to complete the reaction. After the solvent was removed from the reaction mixture under reduced pressure, the concentrate was crystallized from ethanol (5 mL) at room temperature, filtered and washed with ethanol and dried to give the title compound (0.520 g, 66.8%) as a white solid.

The synthetic route of 1009102-44-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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. COA of Formula: C9H11Cl2N

Step 2: To a suspension of 4-(4-chloiO-6-(2,2?2-trifluoroethoxy)-l,3,5-triazin-2- ylamino)faenzenesulfonamide from step 1 (1 g, 2.61 mmol) in THF (20 mL) was added l-(4-chlorophenyl)cyclopropanamine, HC1 (0.53 g, 2.61 mmol) and iPr2NEt (1.35 mL, 10.4 mmol). The mixture was heated at reflux condition for 16 hours. The solvent was removed under vacuum. The crude product 4-(4-(l -(4- chlorophenyl)cyclopropylamino)-6-(2}2,2-trifiuoroethoxy)-l,3J5-triazm-2- ylamino)benzenesulfonamide was used directly in the next step without further purification. LC-MS (Condition A), MS m/z 514.9 (M+ +H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1009102-44-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; MULL, Eric; ZHAO, Qian; WANG, Tao; ZHANG, Zhongxing; SCOLA, Paul Michael; WO2012/24373; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, belongs to chlorides-buliding-blocks compound, 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 1009102-44-6, category: chlorides-buliding-blocks

To a solution of the intermediate 16 (10 g, 1 S.5 mmoi), 1 -(4-chlorophenyl) cyclopropanamine hydrochloride (4.15 g, 20.34 mmol), and HATU (14.06 g, 37 mmol) in DMF (35 mL) was added DIPEA (12.92 mL, 74 mmol) at 0 C. The reaction mixture was stirred at room temperature for 1 h. After the pH of the reaction mixture was adjusted to 3-4 with 2 N HCI, the resulting precipitates were collected and washed with water (600 mL). The obtained solid was dissolved in DC , and the solution was dried over sodium sulfate. DCM was removed by rotary evaporation under reduced pressure to provide a crude product, which was taken up in PE/EtOAc/DCM (10/1/1 ) to afford the intermediate 14-6 (1 1 g, 15.16 mmol, 82 %) as a solid. LC/MS: m/z calculated 689.4, found 690.3 (M+1 )+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXOSMITHKLINE LLC; GAO, Daxin; HAN, Nianhe; JOHNS, Brian; JIN, Zhimin; NING, Fangxian; TANG, Jun; WU, Yongyong; YANG, Heping; WO2013/20245; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1009102-44-6,Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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.

[00142] To a solution of (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11 bR,13aS)-9~hydroxy-1- isopropyI-5a, 5b, 8,8,11a-pentamethyl-2-oxo- 3,3a,4,5,5a,5b,6,7,7a,8,9,10,11 ,11a,11 b,12,13,13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)-2-methylacrylic acid (350 mg, 0.685 mmol), 1-(4- chlorophenyl)cyciopropanamine hydrochloride (154 mg, 0.754 mmol) and HATU (521 mg, 1.371 mmol) in DMF (2 mL) stirred at 0C was added DIPEA (0.479 mL, 2.74 mmol). The reaction mixture was stirred at 20C for 1 h. The reaction mixture was pH adjusted to 3-4 with 2 M HCI and filtered. The solid was washed with water (50 mL), dissolved into DCM, dried over sodium sulfate and evaporated in vacuo to give the crude (E)-N-(1-{4- chlorophenyl)cyclopropyl)-3-((3aS,5aR,5bR,7aR,9S, 1 1 aR, 1 1 bR, 13aS)-9-hydroxy-1 – isopropyl-5a,5b,8,8,11 a-pentamethyl-2-oxo- 3,33,4,5,53,5^6,7,73,8,9, 10,11 ,1 1 a, 1 1 b, 12, 3, 3a-octadecahydro-2H- cyciopenta[a]chrysen-3a-yI)-2-methylacrylamide (650 mg, 0.680 mmol, 99 %) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAN, Nianhe; JOHNS, Brian, A.; TANG, Jun; WO2013/91144; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1009102-44-6,Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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.

Step 2:To a solution of methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)- 1 ,3,5-triazin-2- ylamino)benzoate (870 mg, 2.4 mmol) from Step 1 in THF (10 mL) was added l-(4- chlorophenyl)cyclopropanamine, HC1 (500 mg, 2,450 mmol) and Hunig’sBase (1.677 mL, 9.60 mmol). The resulting mixture was stiiTed for 16 h. The precipitate was filtrated through a plug washing with THF to give acrude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.1 g of the desired product as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; MULL, Eric; ZHAO, Qian; WANG, Tao; ZHANG, Zhongxing; SCOLA, Paul Michael; WO2012/24373; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1009102-44-6, 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. 1009102-44-6 name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, This 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.

[00108] To a soution of (E)-3-((3aS,5aR,5bR,7aR,9S> 11 aR, 11 bR, 13aS)-9-hydroxy-1 – isopropyl-5a,5b,8,8,1 1 a-pentamethyl-2-oxo- 3,33,4,5,53,5^6,7,78,8,9,10,11 ,11a,11 b,12,13,13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)acrylic acid (500 mg, 1.007 mmol), 1-(4- chlorophenyl)cyclopropanamine hydrochloride (226 mg, 1.107 mmol) and HATU (765 mg, 2.013 mmol) in Nu,Nu-dimethylformamide (DMF) (2 ml_) stirred at 0C was added DIPEA (0.703 mL, 4.03 mmol) . The reaction mixture was stirred at 20 C for 1 h. The reaction mixture was adjusted pH to 3~4 by 2 M HCI, filtered, and the solid was washed with water (50 mL), solved into DCM, dried over sodium sulfate and evaporated in vacuo to give the crude product. The crude product was washed with petrol ether/EtOAc/DCM (10/1/1) to afford the target product (E)-N-(1-(4-chlorophenyl)cyclopropy)-3- ((3aS,5aR,5bR,7aR,9S, 11 aR, 1 1 bR, 13aS)-9-hydroxy-1 -isopropyl-5a,5b,8,8, 11 a- pentamethyl-2-oxo-3,3a,4, 5, 5a, 5b,6,7,7a,8,9, 10, 11 , 11 a, 1 1 b, 12, 13, 13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)acrylamide (685 mg, 1.007 mmol, 100 %)) as a yellow soild.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAN, Nianhe; JOHNS, Brian, A.; TANG, Jun; WO2013/91144; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1009102-44-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1009102-44-6 as follows.

To a solution of (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1- isopropyl-5a,5b,8,8, 11 a-pentamethyl-2-oxo- 3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a, 11b, 12,13, 13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)-2-methylacrylic acid (350 mg, 0.685 mmol), 1-(4- chlorophenyl)cyclopropanamine hydrochloride (154 mg, 0.754 mmol) and HATU (521 mg, 1.371 mmol) in DMF (2 mL) stirred at 0C was added DIPEA (0.479 ml_, 2.74 mmol). The reaction mixture was stirred at 20C for 1h. The reaction mixture was pH adjusted to 3-4 with 2 M HCI and filtered. The solid was washed with water (50 mL), dissolved into DCM, dried over sodium sulfate and evaporated in vacuo to give the crude (E)-N-(1-(4- chlorophenyl)cyclopropyl)-3-((3aS,5aR,5bR,7aR,9S, 11 aR, 11 bR, 13aS)-9-hydroxy-1 – isopropyl-5a,5b,8,8, 11 a-pentamethyl-2-oxo- 3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a, 11b, 12,13, 13a-octadecahydro-2H- cyclopenta[a]chrysen-3a-yl)-2-methylacrylamide (650 mg, 0.680 mmol, 99 %) as a yellow solid.

According to the analysis of related databases, 1009102-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAN, Nianhe; JOHNS, Brian Alvin; TANG, Jun; WO2013/90683; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics