Month: March 2021

These common heterocyclic compound, 41965-95-1, name is 3-Chloro-4-methoxybenzylamine 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. Recommanded Product: 41965-95-1

Example 3 : 10- [(3-chloro-4-methoxybenzyl)amino] -2-ethyl- 1 ,2,3,4- tetrahydrobenzo [b] [ 1 ,6] naphthyridine-8-carbonitrile [00151] A mixture of 5 (0.18 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (0.18 mmol), Nal (0.009 mmol), and phenol (0.18 mmol) was heated at 130 C for 2.5 h (Scheme 4). The reaction mixture was diluted with Et20 (30 mL) and washed with IN NaOH (3xlmL). The organic layer was dried over Na2S04, filtered and evaporated under reduced pressure. The residue was purified by Flash Chromatography (5% MeOH in AcOEt) to give the desired compound C (38% of yield). MS ESI (m/z) 407 (M+H)+, 1H NMR (300 MHz, CDC13) delta 8.32 (d, 1H, J= 1.2 Hz), 7.97 (d, 1H, J= 8.7 Hz), 7.71 (dd, lH, Ji= 1.8, J2= 8.7 Hz), 7.37 (d, 1H, J= 2.1 Hz), 7.17 (dd, lH, Ji= 2.1, J2= 8.4 Hz), 6.94 (d, 1H, J= 8.4 Hz), 4.56 (d, 2H, J= 5.7 Hz), 4.12 (br s, 1H), 3.92 (s, 3H), 3.59 (s, 2H), 3.22 (t, 2H, J= 6.0 Hz), 2.87 (t, 2H, J= 6.0 Hz), 2.66 (q, 2H, J= 7.2 Hz), 1.18 (t, 3H, J= 7.2 Hz).

The synthetic route of 3-Chloro-4-methoxybenzylamine Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
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Electric Literature of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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.

General procedure: To the solution of acid in 55 DMF (7ml), were added 56 EDC.HCl (1mmol) and 57 HOBt (1mmol) respectively at 0C. The solution was stirred for 30min followed by addition of 58 (S)-1-phenylethan-1-amine (0.8mmol) and 59 NEt3 (1.33mmol). The reaction mixture was stirred for 1h at 0C and then for 12hat room temperature. The reaction mixture was quenched by saturated NaHCO3 and then extracted with EtOAc. The organic layer was dried with Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography to obtain pure 60 15a.

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karale, Uttam B.; Krishna, Vagolu Siva; Krishna, E. Vamshi; Choudhari, Amit S.; Shukla, Manjulika; Gaikwad, Vikas R.; Mahizhaveni; Chopra, Sidharth; Misra, Sunil; Sarkar, Dhiman; Sriram, Dharmarajan; Dusthackeer, V.N. Azger; Rode, Haridas B.; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 315 – 328;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 918538-05-3, 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. 918538-05-3 name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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.

1A. Preparation of 2-chloro-N-(3-ethyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine To a mixture of 3-ethyl-1H-pyrazol-5-amine (100 mg, 0.9 mmol) in isopropylalcohol (1 mL), was added 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (120 mg, 0.64 mmol) and DIEA (0.1 mL, 0.64 mmol). The reaction mixture was stirred at room temperature overnight. The precipitated product was filtered and washed with cold i-PrOH. The solid was dried under N2 overnight to give the title compound. (118 mg, 71%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 26487-67-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 27: Synthesis of (4-methoxyphenyI)(naphthalen-l-yl)methanone O- 2-(azepan-l-yl)ethyl oxime oxalate (Compound 6g). Into a 50 ml round bottom flask, 4-(methoxy phenyl (naphthalen-l-yl)methanone oxime (1 mmole, 277 mg), l-(2-Chloro-ethyl)-azepane hydrochloride (1.2 mmole, 237.6 mg), baked K2C03 (5 mmole, 690 mg) and dry acetone (10.0 ml) were taken. The reaction mixture was refluxed under anhydrous conditions for 6 hours. The reaction was followed by TLC monitoring. After completion of the reaction, K2C03 was filtered off and washed with acetone (2×10 ml). Filtrate was concentrated and the crude product was purified by basic alumina column chromatography using distilled Hexane to yield the pure product (312mg, 77.61percent). The product obtained was oily so a salt of the compound was prepared. Procedure for oxalate salt formation: Oxalic acid, 1 mmole/ 1 mmole of compound, (97.79 mg) and oily product (312 mg) were dissolved in dry methanol separately into two round bottom flasks. The acid and the compound were mixed and shaken thoroughly. The salt was precipitated using dry diethyl ether, filtered, washed with the same and collected. Yield: 331 mg, 62.69percent. MP. (Oxalate Salt of compound)= 122 ¡ãC; ESI MS(m/z)= 403 (M+H), I (KBr, Cm-1): 3446.5, 2933.9, 2599.9, 1721.6, 1607.9, 1510.2, 1459.5, 1251.3, 1 177.9, 1026.7, 960.1, 719.2; NMR (300MHz, CDC13): delta= 7.92(d, J=8.0 Hz, 2H, ArH), 7.69(d, J=8.2 Hz, 1H, ArH), 7.58-7.39(m, 5H, ArH), 7.33-7.28(m, 1H, ArH), 6.84(d, J=8.5 Hz, 2H, ArH), 4.27(t, J=6.1 Hz, 2H, OCH2), 3.80(s, 3H, OCH3), 2.78-2.67(m, 2H NCH2), 2.5 l(m, 4H NCH2), 1.49(m, 8H, CH2); Analysis calculated for C26H30N2O2: C, 77.58; H, 7.51; N, 6.96; found: C, 77.55; H, 7.53; N, 6.95.

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, 1-(2-Chloroethyl)azepane hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; SANYAL, Sabyasachi; KUMAR, Atul; CHATTOPADHYAY, Naibedya; LAL, Jawahar; TRIVEDI, Arun Kumar; DATTA, Dipak; RATH, Srikanta Kumar; AKHTAR, Tahseen; DWIVEDI, Shailendra Kumar Dhar; YADAV, Manisha; CHAKRAVARTI, Bandana; SINGH, Abhishek Kumar; MISHRA, Jay Sharan; SINGH, Nidhi; TRIPATHI, Anil Kumar; WO2015/29068; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 821-10-3, name is 1,4-Dichlorobut-2-yne, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,4-Dichlorobut-2-yne

General procedure: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketosulfones 1a-p (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at 25 C. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc15/1e8/1) afforded 4a-p.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 821-10-3.

Reference:
Article; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 84859-27-8, name is 5-Chloro-N1-methylbenzene-1,2-diamine, 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. Quality Control of 5-Chloro-N1-methylbenzene-1,2-diamine

6-Chloro-l-methyl-l,3-dihydro-benzoimidazol-2-one (61): A mixture of 4- chloro-N2-methyl-benzene-l,2-diamine (60) (100 mg, 0.64 mmol, 1 eq), triphosgene (95 mg, PATENT Attorney Docket No.: 019934-00601 OUS0.32 mmol, 0.5 eq), TEA (0.26 ml) in THF(2 ml) was stirred at rt for 4 hours. The reaction solution was washed with ethyl acetate and concentrated to provide 6-chloro-l -methyl- 1,3- dihydro-benzoimidazol-2-one (61).

The synthetic route of 5-Chloro-N1-methylbenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2007/22257; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H6BrCl

Method B (+/-)-3-(4-Chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene hydrochloric acid salt A mixture of 5-bromo-2-chlorotoluene (10.0 g, 48.7 mmol) in diethylether (100 ml) was cooled to -700C followed by addition of buthyllithium (21.4 ml, 2.5 M) at -700C. The mixture was stirred at room temperature for 1 h followed by addition of tropinone (6.77 EPO g, 48.7 mmol) at -700C, solved in THF. The mixture was stirred at -700C for 1 h. The mixture was allowed to warm to room temperature. The mixture was made acidic by adding aqueous hydrochloric acid (1 M). The acidic aqueous phase was washed with diethylether (50 ml). The mixture was made alkaline by adding aqueous sodium hydroxide followed by extraction with diethylether (3 x 50 ml). Yield of intermediate (+)- 3-(4-chloro-3-methyl-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol 11.6 g (90%). A mixture of (+/-)-3-(4-chloro-3-methyl-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol (7.5 g, 28.2 mmol) and aqueous hydrogen chloride (37%) was stirred at reflux for 1 h. The mixture was allowed to cool to room temperature and was made alkaline by adding concentrated aqueous ammonia. Yield 6.0 g (86%). The hydrochloric salt was precipitated. Mp 177-179C.

The synthetic route of 54932-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROSEARCH A/S; WO2007/25978; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. SDS of cas: 918538-05-3

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 622-86-6, name is (2-Chloroethoxy)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: (2-Chloroethoxy)benzene

2-(4-Chlorophenyl)butanoic acid (397.3 mg, 2.0mmol) was suspended with stirring in trifluoroacetic anhydride (277.4 uL, 2.0mmol). Then (2-chloroethoxy)benzene (252.4 uL, 1.8 mmol) was added dropwise andthe resulting mixture was stirred at room temperature overnight. The reactionwas quenched with saturated sodium bicarbonate solution (5 mL) and extractedwith ethyl acetate (2 x 15 mL). Thecombined organic layers were dried over anhydrous magnesium sulfate andconcentrated on a rotary evaporator. Theresulting residue was purified by reverse-phased chromatography (C-10 column,gradient of acetonitrile in water with 0.1% trifluoroacetic acid) to afford297.1 mg (49%) of the desired product as a yellow solid. 1H NMR (400 MHz, MeOD) delta 7.99 (d,J = 8.9 Hz, 2H), 7.28 (m, 4H), 6.96 (d, J = 8.9 Hz, 2H), 4.58 (t, J = 7.2Hz,1H), 4.27 (t, J = 5.5 Hz, 2H), 3.84 (t, J = 5.5 Hz, 2H), 2.11 (m, 1H), 1.78(m, 1H), 0.88 (t, J = 7.3 Hz 3H); MS (ESI) (m/z) 318.1/320.1 (M+H)+.

The synthetic route of 622-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Childers, Wayne; Fan, Rong; Martinez, Rogelio; Colussi, Dennis J.; Melenski, Edward; Liu, Yuxiao; Gordon, John; Abou-Gharbia, Magid; Jacobson, Marlene A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4535-90-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 30 trans-(2-{8-Chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl}-ethyl)-methyl-amine A mixture of trans-8-chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.130 mmol), cesium carbonate (170 mg, 0.521 mmol) and 2-methylaminoethyl chloride hydrochloride (67.7 mg, 0.521 mmol) in acetonitrile (1.3 ml) was heated at 70 C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the hydroformate salt of the title compound, which was liberated by filtration over aminopropyl modified silica gel (10 g) with methanol (20 ml) as eluent. The filtrate was concentrated to dryness. The residue was redissolved in ethyl acetate, filtrated over cotton wool and concentrated to dryness to give the title compound (38 mg, 66%) as off-white solid. MS m/e: 441 ([M+H]+).

The synthetic route of 2-Chloro-N-methylethanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dolente, Cosimo; Schnider, Patrick; US2011/275801; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics