Category: amides-buliding-blocks

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,
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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,
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. 96-72-0, name is 2-Chloro-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H5ClN2O4S

The compound 4 (14.15 g, 59.8 mmol) and 300 mL of methanol were placed into a flask and stirred at 50 C until dissolved completely and then 10% Pd/C (1.4 g) was added. The mixture was intensively stirred under H2 at 50 C and monitored with TLC. After 4 h, the reaction was complete, and the suspension was filtered. The resulting solution was evaporated to give the crude product. It was dissolved in 30 mL of 9 mol/L hydrochloric acid solution and filtered. The filtrate was alkalified with 10 mol/L sodium hydroxide solution to pH 7. The suspension was filtered to afford the compound 5 (10.27 g, 83% yield, m.p. 166-167 C). 1H NMR (400 MHz, DMSO-d6) delta (ppm): 7.969 (d, 1H, JH = 8.8 Hz, Ar-H), 8.017 (s, 2H, SO2NH2), 8.414-8.442 (m, 1H, Ar-H), 8.671-8.677 (m, 1H, Ar-H).

According to the analysis of related databases, 96-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pan, Li; Jiang, Ying; Liu, Zhen; Liu, Xing-Hai; Liu, Zhuo; Wang, Gang; Li, Zheng-Ming; Wang, Di; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 18 – 26;,
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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,
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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. 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

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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,1,1-Trifluoro-N-phenylmethanesulfonamide

6- (3-METHOXYPHENYL)-2- (2-MORPHOLIN-4-YL-2-OXOETHYL)-3-HYDROPYRIMIDIN-4-ONE 8 (leq) is dissolved in CH2CL2 in a round bottom flask, oven dried and kept under N2. Triethylamine is added (1.4 eq) followed by N-Phenyl trifluoromethanesulfonimide (1.2 eq) and DMAP (10 mol%). The reaction mixture is stirred at room temperature overnight. The solvent is evaporated under reduced pressure and the residue purified by chromatography on silicagel (ethyl acetate/hexanes 1: 5), obtaining the desired 6- (3-METHOXYPHENYL)-2- (2-MORPHOLIN-4-YL-2-OXOETHYL) pyrimidin-4-yl (trifluoromethyl) sulfonate 9.

According to the analysis of related databases, 456-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIRON CORPORATION; WO2004/48365; (2004); 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

Reference of 316146-27-7, The chemical industry reduces the impact on the environment during synthesis 316146-27-7, name is N-(4-Bromophenyl)-3-phenylpropanamide, I believe this compound will play a more active role in future production and life.

b) Preparation of intermediate 11; The reaction was carried out twice. POCl3 (1.225 mol) was added dropwise at 10¡ãC to DMF (0.525 mol). Then intermediate 10 (0.175 mol) was added at room temperature. The mixture was stirred overnight at 8O0C, poured out on ice and extracted with CH2CI2. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. Yield: 77.62 g of intermediate 11 (67percent).

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, N-(4-Bromophenyl)-3-phenylpropanamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/435; (2007); 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. 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