Tag: M.W=100-200

Application of 4815-28-5,Some common heterocyclic compound, 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, molecular formula is C9H12N2OS, 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: A solution of 2-aminothiophene derivatives 1a-c (0.01 mol) in 7.2 mL conc. HCl and 4 mL H2O was stirred and cooled in ice bath. Then, a solution of NaNO2 (0.690 g,0.01 mol) in 8 mL H2O was added dropwise for 10 min. The cold diazonium solution was added slowly to awell-stirred solution of 3-iminobutanenitrile (0.82 g, 0.01mol) or 1-phenyl-2-thiocyanatoethanone (1.78 g, 0.01mol), in ethanol (60 mL) containing sodium acetate (4 g, 0.05 mol). The reaction mixture was stirred for another3 h. The formed precipitate was filtered off, dried well, and recrystallized from ethanol/benzene to give 3a-c and 7

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, its application will become more common.

Reference:
Article; Gouda, Moustafa A.; Eldien, Hadeer Fakhr; Girges, Margret M.; Berghot, Moged A.; Indian Journal of Heterocyclic Chemistry; vol. 28; 3; (2018); p. 401 – 405;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5349-24-6, 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. 5349-24-6 name is N-Butyl-2-chloroacetamide, 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.

General procedure: Triethylamine (0.3643 g, 3.6 mmol) was added to a solution of the appropriate alkylamine or substituted benzylamine 5a-l (3 mmol) in dichloromethane (7.5 mL), and the reaction mixture was stirred for 5 min at room temperature, then 2-chloroacetyl chloride (0.3857 g, 3.6 mmol) was added dropwise to this reaction mixture at 0 C and stirred for 15 min at room temperature. After completion of the reaction, the solvent was evaporated under reduced pressure to afford 6a-l. KI (0.5976 g, 3.6 mmol) and CTAB (98.40 mg, 7.5% mmol) were added to a solution of the crude product 6a-l in acetone (30 mL) and maintained stirring at reflux for 2 h to afford 7al. K2CO3 (0.2073 g, 3 mmol) was added to a solution of scopoletin (0.3843 g, 2 mmol) in acetone (30 mL), and the reaction mixture was stirred at refluxed for 30 min. Then crude intermediates 7a-l were added into the mixture and maintained reflux for 8-12 h (the reaction progress was monitored by TLC with UV detection). After cooling the reaction and filtration, the solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, washed with saturation sodium bicarbonate, and saturation salt solution successively, dried over anhydrous sodium sulfate, evaporated under reduced pressure to give the target crude products. The crude products were purified by column chromatography using petroleum ether/ethyl acetate from 6:1 to 2:1 as the gradient eluent system to yield the products 26-37.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Butyl-2-chloroacetamide, and friends who are interested can also refer to it.

Reference:
Article; Luo, Jinxiang; Lai, Ting; Guo, Tao; Chen, Fei; Zhang, Linli; Ding, Wei; Zhang, Yongqiang; Molecules; vol. 23; 5; (2018);,
Amide – Wikipedia,
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Synthetic Route of 513-74-6,Some common heterocyclic compound, 513-74-6, name is Ammonium carbamodithioate, molecular formula is CH6N2S2, 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.

0.69g Ammonium dithiocarbamate were dissolved in 10ml MeOH and 1.47g 4-(2- bromoacetyl)-1-methylpyridinium bromide were added. After 2h at ambient temperature the mixture was refluxed. After cooling the precipitate was filtered, washed with MeOH and dried. Yield: 0.15g 1H-NMR (DMSO-d6) delta 4.32(s, 3H), 8.32(s, 1 H), 8.45(d,2H; J=6.9Hz), 9.08(d,2H; J=6.8Hz), 14.1 (br s, 1 H) 13C-NMR (DMSO-c/6) delta 47.3, 121.6, 122.5, 136.6, 141.3, 145.9, 190.2

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

Reference:
Patent; SANDOZ AG; KREMMINGER, Peter; STURM, Hubert; WO2013/34718; (2013); A1;,
Amide – Wikipedia,
Amide – 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. 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

Isopropylmagnesium chloride (2.0 M in THF, 2.0 mL, 3.97 mmol) was added to a solution of 2- bromo-7-fluoro-5-(l-methylpyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazole (0.379 g, 1.32 mmol) and N-methoxy-N-methylcyclopropanecarboxamide (0.529 g, 3.97 mmol) in THF (13.2 mL) at 0C. After 5 min, the reaction was warmed to rt and stirred for an additional lh. Water was added and the reaction was diluted with isopropyl acetate. Brine was added and the aqueous layer was extracted with isopropyl acetate (4 x 50 mL). The combined organic layers were dried with sodium sulfate, concentrated and the crude residue was purified by prep SFC to afford arbitrarily assigned cyclopropyl((5S,7S)-7-fluoro-5-(l -methyl- lH-pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[ 1 ,2- b] [l ,2,4]triazol-2-yl)methanone (44.23 mg, 0.161 mmol, 12% yield). NMR (400 MHz, DMSO-d6) delta 7.80 (d, J = 0.8 Hz, 1H), 7.48 (d, J = 0.8 Hz, 1H), 6.21 (ddd, J= 56.4, 7.0, 2.4 Hz, 1H), 5.66 (ddd, J = 8.2, 6.0, 3.6 Hz, 1 H), 3.81 (s, 3H), 3.73 – 3.55 (m, 1H), 2.99 {XX, J = 7.5, 4.9 Hz, 1H), 2.80 (dddd, J = 26 A, 14.9, 3.7, 2.4 Hz, 1H), 1.14 – 0.95 (m, 4H). LCMS RT = 3.10 min, m/z = 276.1 [M + H]+. Prep SFC Information: Column: Whelko-01 5 muiotaeta, (150 x 21.2 mm), Mobile Phase: Carbon Dioxide (A) / 0.1 % Ammonium Hydroxide in Methanol (B), Elution Program Isocratic: 35% B Flow Rate: 70 mL/min, Column Temperature: 40 C, Wavelength: 220 nm.

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 147356-78-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 360-64-5, The chemical industry reduces the impact on the environment during synthesis 360-64-5, name is 2-(Trifluoromethyl)benzamide, I believe this compound will play a more active role in future production and life.

General procedure: Benzamides 2 (6 mmol) was dissolved in dry THF (20 mL) andthereto was added P2S5 (6 mmol) and heated at 65 C for 3 h, afterwhich the reaction mixture was cooled, poured in NaHCO3 (10%,100 mL), stirred for half an hour, then the resulting solid wasfiltered, dried and recrystallized from ethyl acetate to get compounds3.

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, 2-(Trifluoromethyl)benzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yan, Zhongzhong; Liu, Aiping; Huang, Mingzhi; Liu, Minhua; Pei, Hui; Huang, Lu; Yi, Haibo; Liu, Weidong; Hu, Aixi; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 170 – 181;,
Amide – Wikipedia,
Amide – 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. 617-36-7, name is Ethyl 2-amino-2-oxoacetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H7NO3

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available oxalamic acid ethyl ester (43.429 g, 370.86 mmol) and Lawesson’s reagent (150.00 g, 370.86 mmol) in toluene (550.0 mL) was stirred at 80 0C for 2 h. The resulting mixture was cooled to rt and CH2CI2 (300 mL) was added. The mixture was filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2CI2) gave the title compound as an orange solid.

According to the analysis of related databases, 617-36-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/77990; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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: 16066-84-5

Example 25 2′-(2,6-difluoro-3,5-dimethoxyphenyl)-6′-(methylamino)-1′,2′-dihydro-3’H-spiro[cyclopropane-1,4′-[2,7]naphthyridin]-3′-one To a stirred solution of 6′-chloro-2′-(2,6-difluoro-3,5-dimethoxyphenyl)-1′,2′-dihydro-3’H-spiro[cyclopropane-1,4′-[2,7]naphthyridin]-3′-one (Example 23, Step 6: 90.0 mg, 0.236 mmol) and tert-butyl methylcarbamate (89.5 mg, 0.682 mmol) in 1,4-dioxane (3 mL) were added sequentially dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (BrettPhos, Aldrich, catNo.718742: 24.4 mg, 0.0455 mmol), sodium tert-butoxide (52.4 mg, 0.546 mmol), and palladium acetate (10.2 mg, 0.0455 mmol) at room temperature. The resulting mixture was purged with N2 and heated to 90 C. After stirring for 45 minutes at 90 C., the reaction mixture was cooled to ambient temperature and the volatiles were removed in vacuo. The residue was dissolved in DCM (1 mL) then TFA (1 mL) was added. After stirring at room temperature for 1 hour, the reaction mixture was concentrated and the crude was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/min) to give the desired product (32 mg) as its TFA salt. LC-MS calculated for C19H20F2N3O3 [M+H]+ m/z: 376.1. found 376.2. 1H NMR (500 MHz, DMSO-d6): delta 7.90 (s, 1H), 7.07 (t, J=10.0 Hz, 1H), 6.46 (s, 1H), 4.80 (s, 2H), 3.89 (s, 6H),), 2.90 (s, 3H) 1.79 (dd, J=10.0 Hz, 5.0 Hz, 2H), 1.56 (dd, J=10.0 Hz, 5.0 Hz, 2H) ppm.

The synthetic route of tert-Butyl methylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun, Yaping; Lu, Liang; Yao, Wenqing; Zhuo, Jincong; Wu, Liangxing; Xu, Meizhong; Qian, Ding-Quan; He, Chunhong; Zhang, Fenglei; US2014/315902; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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. name: N,N-Dimethylsulfamide

1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-.; 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).; An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.; To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 oC for 2 h. After cooling to 30 oC, N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 oC. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 oC. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (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 3984-14-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/188458; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, 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 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

To a stirred solution of the appropriate aminothiophene (1 equiv. ) in 1,4-dioxane (5ml per mmol of aminothiophene) was added the appropriate acyl chloride (1.2 equiv. ). The reaction mixture was stirred at room temperature for 17 hours and then diluted with ether or hexane. The resultant precipitate was removed by filtration, washed with ether and air- dried to give the desired product. Compound No. 390 of Table 14 Using the additional general procedure 2- (2-chloroacetylamino)-4, 5,6, 7-tetrahydro- benzo [b] thiophene-3-carboxylic acid amide (Compound No. 390 of Table 14) was obtained from aminothiophene WO as an off-white solid in 52% yield. m. p. 242-245C (dec.).

The synthetic route of 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2005/44008; (2005); A2;,
Amide – Wikipedia,
Amide – 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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C6H6FNO2S

100 mg of 4-fluorobenzensulfonamide (0.71 mmol) dissolved with allylamine (434 muL, 5.71 mmol) in a sealed tube was heated at 110 C for 14 days. Then, the mixture was cooled to room temperature and was diluted with MeOH. The solvent was evaporated and the crude mixture was purified by combi-flash with the eluent petroleum ether/ethylacetate: 70/30, thereby obtaining compound 7 (62 mg, 51%) as an orange solid (mp: 74-76 C). 1H NMR (CD3COCD3, 400 MHz, ppm) d: 3.85 (td, CH2, J = 5.5 Hz, J = 1.7 Hz, H10), 5.12 (ddt, 1H, J = 10.3 Hz, J = 1.6 Hz, J = 1.6 Hz, H3′), 5.26 (ddt, 1H, J = 17.2 Hz, J = 1.8 Hz, J = 1.8 Hz, H3′), 5.89 (broad s, 1H, NH), 5.93 (m, CH, H2′), 6.16 (s, SO2NH2), 6.69 (d, 2CH, J = 8.9 Hz, H3 and H5), 7.60 (d, 2CH, J = 8.9 Hz, H2 and H6). 13C NMR (CD3COCD3, 100 MHz, ppm) d: 46.1 (CH2, C1′), 112.2 (2CH, C3 and C5), 116.1 (CH2, C30), 128.7 (2CH, C2 and C6), 131.7 (C1), 136.1 (CH, C2′), 152.5 (C4). MS (IES+, ACN): m/z 213 [M+H]+. HRMS (ESI, CH3OH): m/z 235.0518 (m/z theoretical: 235.05172) [M+Na]+.

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:
Article; Compain, Guillaume; Martin-Mingot, Agnes; Maresca, Alfonso; Thibaudeau, Sebastien; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry; vol. 21; 6; (2013); p. 1555 – 1563;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics