Category: chlorides-buliding-blocks

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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5ClFN

[00387] Intermediate 32A. (E)-N’-(3-Chloro-2-fluorophenyl)-2- oxopropanehydrazonoyl chloride: To a solution of 3-chloro-2-fluoroaniline (1.511 mL, 13.74 mmol) in HCl (116 mL, 116 mmol) at 0 C was added a solution of sodium nitrite (1.896 g, 27.5 mmol) in water (12 mL) dropwise while maintaining the temperature at 0 C. After completion of addition, the reaction was stirred at the same temperature for additional 30 mins. The pH of the reaction mixture was adjusted to 4.5 using solid sodium acetate. The resultant mixture was then treated dropwise with 3-chloropentane- 2,4-dione (2.129 mL, 17.86 mmol) in methanol (12 mL). After completion of addition, the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water and then extracted with ether. The crude product was then purified by silica gel chromatography to isolate the desired product. MS(ESI) m/z: 249.0 (M+2H)+.

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 2106-04-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
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4152-90-3, name is (3-Chlorophenyl)methanamine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C7H8ClN

A solution of 8-chloro-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-[1,2,4]triazolo[4, 3-a]pyrazine (500 mg, 1.60 mmol), (3-chlorophenyl)methanamine (0.39 mL, 3.2 mmol) and TEA (0.68 mL, 4.8 mmol) in EtOH (8.0 mL) was stirred at 80° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with DCM and washed with water and brine. The separated organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by MPLC on SiO2 (2-5percent MeOH in DCM) to give N-(3-chlorobenzyl)-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-amine (2.40 g, 90percent) as a yellow oil. 1H-NMR (CDCl3, 400 MHz): delta 7.41 (m, 2H), 7.27 (m, 3H), 7.24 (d, J=4.8 Hz, 1H), 5.75 (d, J=5.2 Hz, 1H), 5.31 (t, J=4.0 Hz, 1H), 4.62 (s, 1H), 2.95 (m, 2H), 1.59 (s, 3H), 1.42 (s, 3H).

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; Lee, Jin-Hwa; Kim, Seung-Yong; Kim, Do-Ran; Ahn, Koo-Hyeon; Lee, Gwi-Bin; Kim, Doo-Seop; Hwang, Hyun-Sook; (74 pag.)US2017/204101; (2017); A1;,
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Reference of 62593-17-3, A common heterocyclic compound, 62593-17-3, name is 2,4-Dichloro-6-(trifluoromethyl)aniline, molecular formula is C7H4Cl2F3N, 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 a suspension of CuCl2 (3.0 mmol) in 30 mL CH3CN was added tBu-nitrite (4.1 mmol) followed by dropwise addition of 1,1-dichloroethylen (39.1 mmol). A solution of 2,4-dichloro-6-trifluoromethylaniline (2.2 mmol) in 2 mL CH3CN was slowly added. After stirring at RT overnight, the reaction was quenched with 25percent aqueous HCl solution and extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4. After removal of the solvent the crude was redissolved in 3 mL MeOH. After addition of 2.4 mL of a 30percent solution of NaOMe in MeOH the mixture was refluxed for 5 h. Then, 1.8 mL concentrated H2SO4 solution was added at RT and the mixture was heated to reflux for 1 h. After concentrating in vacuo the resulting solid was partitioned between water and DCM. The water phase was extracted 3 times with DCM. The combined organic layers were dried over MgSO4. Purification with CC using Hept/EtOAc (10/1) gives the desired product as yellowish oil. _LC-MS (A): tR=0.93 min; 1H NMR ((CD3)2SO) delta: 8.11 (s, 1H), 7.88 (s, 1H), 3.97 (s, 2H), 3.65 (s, 3H).

The synthetic route of 62593-17-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Hilpert, Kurt; Hubler, Francis; Kimmerlin, Thierry; Renneberg, Dorte; Stamm, Simon; US2015/25075; (2015); A1;,
Chloride – Wikipedia,
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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. 14862-52-3, name is 3,5-Dibromochlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 14862-52-3

General procedure: 4-fluoroaniline (1.1 g, 0.010 mol) Pd (dba) 2 (0.5 g, 0.010 mol) was added to intermediate 1-6 (2.6 g, 0.010 mol)0.0005 mol), sodium tert-butoxide (1.9 g, 0.020 mol) was added 70 mL of TOL,Followed by stirring for 4 hours. After the completion of the reaction, column purification was performed on H20: MC and column purification (n-HEXANE: MC) to obtain 2.6 g (77%) of 1-7 Intermediate 2-1 (3.0 g, 0.010 mol) was added to 1,3-dibromo-5-chlorobenzene (2.7 g, 0.010 mol)Was synthesized in the same manner as in Example 1- (7) to give 5.4 g (yield 75%) of Intermediate 6-1

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 14862-52-3.

Reference:
Patent; P&H Tech Co.,Ltd; Hyun, Seo Yong; Jung, Sung Wook; Kim, Dong Won; (133 pag.)KR2016/54866; (2016); A;,
Chloride – Wikipedia,
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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 1939-99-7 as follows. Recommanded Product: 1939-99-7

Example 95 Preparation of t-Butyl (3-Benzylsufonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetate STR115 Collidine (0.59 mL, 4.5 mmole) was added in one portion to a stirred solution of the compound of Example 94 (0.89 g, 3.7 mmole) and benzylsulfonyl chloride (0.86 g, 4.5 mmole) in acetonitrile (20 ml) cooled in an ice bath. The solution was stirred for 5 minutes at 0 C., followed by 45 min at room temperature. The reaction mixture was quenched with water, then diluted with ethyl acetate (100 mL), washed with 3% HCl (until aqueous layer is pH 1), and brine, dried over magnesium sulfate, and the solvent was removed. The residue was dissolved in methanol, concentrated to a volume of approximately 3 mL, and the product was precipitated with the addition of diethyl ether. The precipitate was filtered to give 0.67 g of the title compound. The filtrate was concentrated and chromatographed on flash silica gel using 20-67% ethyl acetate hexanes as eluent. An additional 0.20 g of the title compound was recovered. A total of 0.87 g of the title compound (59% yield) was recovered. Rf=0.29 (silica gel, 33% ethyl acetate/hexanes).

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvas International, Inc.; US5658930; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 53531-69-4, 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. 53531-69-4 name is (4-Bromophenyl)methanesulfonyl chloride, 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.

To a stirred solution of (4-bromophenyl)methanesulfonyl chloride (DC; 500 mg, 1.85 mmol) in pyridine (10 mL) under inert atmosphere was added morpholine (712 mg, 2.22 mmol) at RT and stirred for 16 h. The reaction was monitored by TLC. After complete consumption of the starting material, the reaction mixture was diluted with water (30 mL) and was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (15 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by silica gel column chromatography (20-30% EtOAc/hexanes) to afford DD (360 mg, 61%) as a white solid. *H NMR (400 MHz, CDC13): delta 7.53 (d, J = 8.8 Hz, 2H), 7.29 (d, / = 8.8 Hz, 2H), 4.16 (s, 2H), 3.65 (t, / = 4.8 Hz, 4H), 3.13 (t, 7 = 4.8 Hz, 4H).

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

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, William, J.; YATES, Christopher, M.; RAFFERTY, Stephen, W.; WO2014/117090; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 108-37-2, 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. 108-37-2, name is 1-Bromo-3-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (76 mL, 0.4 mol) in anhydrous THF (664 mL) and n-hexane (220 mL) was added 2.5 M n-BuLi (160 mL, 0.4 mol) dropwise at -78 0C over 1 h. The mixture was stirred for 1 h at -78 0C and a solution of 1-bromo- 3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added dropwise at – 78 0C. After stirring for an additional 1 h at the same temperature, a solution of iodine (101 g, 0.4 mol) in anhydrous THF (400 mL) was added dropwise at -78 0C. The temperature was raised from -78 0C to rt during 2 h. After stirring for 18 h at rt, the mixture was concentrated in vacuo to give the crude product (120 g) which was distilled under reduced pressure to give l-bromo-3-fluoro-2-iodobenzene (115 g, 91%). 1H NMR (400MHz, CDCl3): 7.12-7.18 (t, IH), 7.35-7.41 (dd, IH), 7.49-7.54 (dd, IH); MS (E/Z): 317 (M+H+)

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124575; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1005-56-7,Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

95) 8-Bromo-2′-phenoxythiocarbonyladenosine-3′,5′-cyclic boranophosphate, Sp- isomer (Sp-8-Br-2′-PTC-cAMPB. No. 306)A solution of 5 muiotatauiotaomicronIota of Sp-8-Br-cAMPB (example 2) in 2 ml of dry dichloromethane was treated with 2.5 mg of dimethylaminopyridine (Aldrich) and 1 .4 muIota of phenoxythiocarbonyl chloride (Fluka) for 16 h at RT under argon. The decrease of the starting material at 1 :62 min was followed by HPLC (RP-18, 20 Vol.-% acetonitrile, 20 mM triethylammonium formate buffer, 1 .5 ml/min., pH 7 at 259 nm).The peak for Sp-8-Br-2′-PTC-cAMPB at 2:69 min was isolated by semipreparative column chromatography on reversed phase silica (RP-18, 40 Vol.-% acetonitrile, 20 mM triethylammonium formate buffer, 1 .5 ml/min., pH 7), yield 87.6%.C17H18BBrN506PS; MW 542.1 1 UV: max: 259 nm HPLC: 2:69 min.ESI-MS (+): m/z 643/645 [M + 2TEA + H] +^ 629 [M + 2TEA – BH3 + H] + ESI-MS (-): m/z 540/542 [M – H]? 526 [M – BH3 – H] ~ ^ 212 [8-Br-A – H] +

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLOG LIFE SCIENCE INSTITUTE FORSCHUNGSLABOR UND BIOCHEMICA-VERTRIEB GMBH; GENIESER, Hans-Gottfried; WO2012/130829; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 39226-96-5

Example 12 lambda/-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(3- pyridinyl)-4-imidazolidinecarboxamide (E12); A mixture of crude 3-methyl-2-oxo-1-(3-pyridinyl)-4-imidazolidinecarboxylic acid (0.8 mmol), 1-hydroxybenzotriazole hydrate (147 mg, 0.96 mmol), 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (184 mg, 0.96 mmol), and N-ethyl morpholine (0.307 ml, 2.4 mmol) in dichloromethane (15 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (168 mg, 0.8 mmol) in dichloromethane (1 ml) was added and the reaction stirred at room temperature for 4 hours. The mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution. The organic phase was separated, washed with water and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC. The solid was dissolved in methanol (5 ml) and anhydrous HCI in ether (1 M, 0.5 ml) was added and the solution was evaporated. The resulting solid was collected, washed with ether and dried to give a pale yellow solid. The solid was dissolved in methanol and applied to a SCX ion exchange cartridge and washed with methanol and then 2M ammonia in methanol. The basic fractions were combined and evaporated and the resulting residue was triturated with ether, collected and dried to give lambda/-{[2-Chloro-3- (trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(3-pyridinyl)-4- imidazolidinecarboxamide (27 mg, 8%). LC/MS [M+H]+ = 413, retention time = 1.96 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 13918-92-8 as follows. Recommanded Product: 13918-92-8

General procedure: To 5-(5-(5-Aminopyridin-3-yl)thiophen-2-yl)-2-methyl- isoindolin-1-one (49) (225 mg, 0.79 mmol) in dry pyridine (23 mL) under N2 at RT,was added dropwise, 2,4-difluorobenzenesulphonyl chloride (336 mg, 1.58 mmol) in CH2Cl2(3 mL) over 5 min. The suspension was heated to 45 C under N2 for 4 h., at which pointanother portion of 2,4-difluorobenzenesulphonyl chloride (169 mg, 0.79 mmol) in CH2Cl2 (2mL) was added. The whole mixture was left to stir for at 45 C under N2 for 16 h., then thesolvent removed under reduced pressure. The resulting residue was suspended in acetone (10mL), 1 M HCl (20 mL) added, and the entire mixture stirred for 10 minutes. The solid wasthen collected by filtration, washed well with 1 M HCl and water, dried, and purified bychromatography as described below. In cases where the bis-sulphonamide was also formed, a second step was introduced wherethe crude product above was treated with a 1:1 mixture of 1,4-dioxane and 2 M NaOH. Thecrude sulphonamide resulting from subsequent acidification of the reaction mixture wasisolated by filtration, washed well with water, and dried. Purification was carried out by flashcolumn chromatography (2% MeOH/CH2Cl2 as eluant), giving the title compound as a paleyellow solid (211 mg, 545).

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics