Category: amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 180079-94-1, name is tert-Butyl 3-aminophenethylcarbamate, belongs to amides-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 180079-94-1, Formula: C13H20N2O2

Production Example 30 Production of 3′,4′-dihydro-2’H-spiro[cyclobutane-1,1′-isoquinolin]-6′-amine 2 mL of 85 % phosphoric acid was added to 350 mg of the compound obtained in Production Example 29-2), and stirred at 70C for 1 hour. Further, 0.144 mL of cyclobutanone was added to it, and reacted at 140C for 3 hours, using a microwave reactor. The reaction liquid was diluted with water, then potassium carbonate was added to it, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The crude product was purified through basic silica gel column chromatography (hexane/ethyl acetate) to obtain 157 mg of the entitled compound as a colorless oily compound. 1H-NMR (CDCl3) delta: 7.28 (1H, d, J=8.3 Hz), 6.59 (1H, dd, J=8.3, 2.9 Hz), 6.37 (1H, d, J=2.4 Hz), 3.54 (2H, s), 3.03 (2H, t, J=5.9 Hz), 2.68 (2H, t, J=6.1 Hz), 2.47-2.40 (2H, m), 2.18-2.07 (3H, m), 2.02-1.92 (1H, m)

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, tert-Butyl 3-aminophenethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6325-93-5, name is 4-Nitrobenzenesulfonamide, belongs to amides-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 6325-93-5, HPLC of Formula: C6H6N2O4S

General procedure: A mixture of nitroarene (1 mmol), PdCu/graphene (6 mg) and sodium borohydride (2 mmol) were taken in a 25 mL reaction tube. 3 mL of EtOH:H2O (1:2 in volume ratio) was added by a syringe at 0 C. After 10 min the reaction mixture was placed in an oil bath at 50 C. The reaction was monitored by TLC. On completion, the reaction mixture was extracted with ethylacetate and dried ove ranhydrous Mg2SO4. Evaporation of the combined organic layer andfollowed by column chromatography over silica gel (60-120 mesh) afforded desired corresponding amines.

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Reference:
Article; Feng, Yi-Si; Ma, Jing-Jing; Kang, Yu-Mei; Xu, Hua-Jian; Tetrahedron; 36; (2014); p. 6100 – 6105;,
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Adding a certain compound to certain chemical reactions, such as: 1943-79-9, name is Phenyl methylcarbamate, belongs to amides-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 1943-79-9, Recommanded Product: 1943-79-9

Production Example 19-7 5-((2-Aminopyridin-4-yl)oxy)-6-(difluoromethoxy)-N-methyl-1H-indole-1-carboxamide 4-((6-(Difluoromethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine described in Production Example 19-6 (4.4 mg, 0.015 mmol) was dissolved in N,N-dimethylformamide (500 muL), then 50-72% oily sodium hydride (4.1 mg) was added under nitrogen atmosphere at 0 C., and the mixture was stirred at room temperature for 30 minutes. The mixture was cooled to 0 C. again and phenyl methylcarbamate described in Production Example 1-7 (16.4 mg, 0.108 mmol) was added, and the mixture was stirred at room temperature for 50 minutes. Water and ethyl acetate were added to the reaction mixture for partition. The organic layer was washed with a saturated saline solution, then dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1-0:1-ethyl acetate_methanol=99:1-9:1), and then the target fraction was concentrated under vacuum to obtain the title compound (4.3 mg, 82%). 1H-NMR Spectrum (CDCl3) delta (ppm): 3.08 (3H, d, J=4.8 Hz), 4.44 (2H, brs), 5.49 (1H, brs), 5.91 (1H, d, J=1.8 Hz), 6.26 (1H, dd, J=6.2, 2.2 Hz), 6.50 (1H, t, J=74.0 Hz), 6.61 (1H, d, J=3.7 Hz), 7.35 (1H, s), 7.41 (1H, d, J=3.7 Hz), 7.92 (1H, d, J=5.9 Hz), 8.23 (1H, s).

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; Eisai R&D Management Co., Ltd.; Funasaka, Setsuo; Okada, Toshimi; Tanaka, Keigo; Nagao, Satoshi; Ohashi, Isao; Yamane, Yoshinobu; Nakatani, Yusuke; Karoji, Yuki; US2014/235614; (2014); A1;,
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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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 85006-25-3

To a suspension of sodium hydride (60% in mineral oil, 10 mg, 0.250 mmol) in 0.5 mL of DMF , N,O-diBoc-hydroxylamine (55.6 mg, 0.230 mmol) was added. The mixture was stirred for 30′ at 0C then a solution of 3-[3′- Adamantan-1 -yl-4′-(2-bromo-ethoxy)-biphenyl-4-yl]-acrylic acid ferf-butyl ester (103 mg, 0.192 mmol) in 2 mL of DMF was slowly added. After having stirred at room temperature overnight, DMF was evaporated, the residue was poured into saturated solution of NH4CI and extracted with ethyl acetate. The organic phase was dried and evaporated. Purification by flash chromatography (Hexane/Ethyl acetate 90:10) gave 109 mg (81 %) of the desired compound as white solid; m.p. 165C, Rf(Hexane/Ethyl acetate 90:10) 0.26.1H-NMR (300 MHz, CDCI3) delta:7.61 (1 H, d, J = 16.1 Hz); 7.57.7.50 (4H, m); 7.47 (1 H, d, J = 2.21 Hz); 7.39 (1 H, dd, J = 8.46, 2.21 Hz); 6.93 (1 H, d, J = 8.46 Hz); 6.38 (1 H, d, J = 16.1 Hz); 4.27-4.17 (2H, m); 4.16-4.01 (2H, m); 2.22-2.02 (9H, m), 1 .86- 1 .70 (6H, m), 1 .54 (9H, s); 1 .52 (9H, s); 1.49 (9H, s).

The synthetic route of 85006-25-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEM S.CA.R.L.; PISANO, Claudio; DALLAVALLE, Sabrina; CINCINELLI, Raffaella; MERLINI, Lucio; (56 pag.)WO2018/60354; (2018); A1;,
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Electric Literature of 53250-82-1, 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. 53250-82-1, name is 4-(Methylsulfonamido)aniline belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Take a 250mL three-necked bottle, add 1.86g of p-methylsulfonylaminoaniline, 0.22g of palladium acetate and 1.00g of molecular sieve.2.04 g of methyl 2-oxopropanoate, 0.60 g of acetic acid and 100 mL of dimethyl sulfoxide were injected, followed by a 200 mL oxygen balloon, and stirred at 70 C for 18 hours.After the reaction was completed, 200 mL of ethyl acetate was added to dilute the reaction solution, and the filtered saline 100 mL was washed twice.The organic phase was separated and the aqueous phase was extracted 1time with ethyl acetate.Column chromatography yielded 2.15 g of pure methyl 5-methanesulfonylamino-1H-indole-2-carboxylate in a yield of 80%.

The synthetic route of 4-(Methylsulfonamido)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ren Long; Tang Yanbo; Yang Ying; (27 pag.)CN109748840; (2019); A;,
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Synthetic Route of 104060-23-3, A common heterocyclic compound, 104060-23-3, name is N-Boc-2-(4-Aminophenyl)ethanol, molecular formula is C13H19NO3, 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.

Compound 11A (2.5 g, 10.5 mmol, 1.00 equiv) was dissolved in 25 mL of DCM then cooled to -78C. A Dess-Martin Periodinane solution (DMP, 6.71 g, 15.8 mmol, 1.5 equiv) in DCM (10 mL) was added drop-wise. The cold bath was removed and agitation continued for 1 hour at ambient temperature. The reaction was neutralised with60 mL of a 50/50 mixture of sodium bicarbonate-saturated aqueous solution and Na2S2O3-saturated aqueous solution. The resulting solution was extracted 3 times with 30 mL of EtOAc. The organic phases were combined, washed twice with NaC1- saturated aqueous solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel (EtOAc/PE1/15) to yield 1.0 g (40 %) of compound 11B in the form of a pale yellow solid.

The synthetic route of 104060-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
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Related Products of 1172623-95-8,Some common heterocyclic compound, 1172623-95-8, name is tert-Butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, molecular formula is C12H20N2O4, 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.

Under N2 protection, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 ml), cooledto -10C or lower in an ice salt bath, and a solution of isopropyl magnesium chloride/lithium chloride in tetrahydrofuran(66 ml, 1.3 mol/l) was added dropwise, followed by stirring at about -10C for 1 hour. 1D (10 g, 39 mmol) was dissolvedin dry tetrahydrofuran (100 ml), and added dropwise to the reaction solution while the temperature was maintained at-10C. When the addition was complete, the reaction was allowed to proceed at room temperature for 4 hours. Thetemperature was lowered to about -10C, and a saturated ammonium chloride solution (40 ml) was added dropwise,followed by stirring for 10 min. The pH was adjusted to 5 to 6 with a 3 mol/l hydrochloric acid solution, to allow settlingand partitioning. The aqueous phase was extracted with methyl t-butyl ether (50 ml32). The organic phases werecombined, washed with a saturated sodium chloride solution (30 ml32), dried by addition of anhydrous sodium sulfatethereto, filtered, concentrated, and separated by column chromatography (petroleum ether/ethyl acetate (v/v) = 50:1 to8:1), to obtain a light yellow solid 1E (10.1 g, yield 83.5%).MS m/z (ESI): 210.1 [M-99].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, its application will become more common.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
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Synthetic Route of 38267-76-4, A common heterocyclic compound, 38267-76-4, name is tert-Butyl ethylcarbamate, molecular formula is C7H15NO2, 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.

Ethylamine hydrochloride (2.81 g, 34.5 mmol) and triethylamine (14.4 mL, 103 mmol) were dissolved in CH2Cl2 (100 mL), and cooled on ice. A solution of di-t-butyl dicarbonate (7.69 g, 35.2 mmol) in CH2Cl2 (15 mL) was added, and stirred at room temperature for 14.5 h. The mixture was diluted with CH2Cl2, washed twice with 5% aqueous HCl solution, once with saturated aqueous NaHCO3 solution,dried over anhydrous magnesium sulfate, and evaporated to give crude t-butyl ethylcarbamate (4.36 g, 87%). Crude t-butyl ethylcarbamate (3.77 g, 26.0 mmol) and allyl bromide (4.5 mL, 52.0 mmol) were dissolved in DMF (87 mL), and cooled on ice. NaH (60% in oil, 2.23 g, 55.8 mmol) was added, and stirred at room temperature for 4.5 h. After cooled on ice, the reaction was quenched by adding water. The mixture was diluted with Et2O, washed with 5% aqueous Na2S2O3 solution and saturated aqueousNaHCO3 solution, dried over anhydrous magnesium sulfate, and evaporated. Purification by column chromatography (n-hexane : EtOAc = 30 : 1 v /v), and distillation (3.0 kPa, 89 C) gave 42d (1.73 g, 36%) as colorless liquid. 1HNMR (400 MHz, CDCl3) delta 1.08 (t, J = 7.2 Hz, 3H), 1.46 (s, 9H), 3.05 (br, 2H), 3.70~3.90 (br, 2H). 13CNMR (100 MHz, CDCl3) delta 13.45, 28.43, 49.06, 79.22, 115.92, 155.37. IR (neat) 2976, 1698 cm-1.

The synthetic route of 38267-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Honzawa, Shinobu; Uchida, Mitsuaki; Tashiro, Takuya; Sugihara, Takumichi; Heterocycles; vol. 95; 2; (2017); p. 994 – 1029;,
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Application of 1015-89-0, These common heterocyclic compound, 1015-89-0, name is Phenanthridin-6(5H)-one, 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.

Phenanthridin-6(5H)-one (1; 0.100 g, 0.492 mmol) was placed in aSchlenk flask under argon. POCl3 (3.29 g, 2 mL, 21.4 mmol, 43 equiv)was added, and the mixture was stirred at 100 C for 24 h. The mixturewas cooled, poured onto ice, and stirred for 15 min. The solidthat formed was collected by filtration, washed thoroughly with H2O,and dried in vacuum to give a light-brown solid; yield: 95.5 mg (87%);Rf = 0.65 (hexane-EtOAc, 5:1; detection: UV).IR (KBr): 3103, 3072, 3039, 1613, 1574, 757 cm-1.1H NMR (600 MHz, acetone-d6): delta = 7.69 (ddd, J = 8.2, 7.0, 1.4 Hz, 1 H,H-12), 7.75 (ddd, J = 8.2, 7.0, 1.5 Hz, 1 H, H-13), 7.77 (ddd, J = 8.2, 7.0,1.2 Hz, 1 H, H-4), 7.91 (ddd, J = 8.3, 7.0, 1.3 Hz, 1 H, H-5), 8.10 (ddd,J = 8.2, 1.4, 0.6 Hz, 1 H, H-14), 8.48 (ddd, J = 8.2, 1.3, 0.6 Hz, 1 H, H-3),8.54 (ddt, J = 8.3, 1.5, 0.6 Hz, 1 H, H-11), 8.62 (ddt, J = 8.3, 1.2, 0.3 Hz, 1H, H-6).13C NMR (151 MHz, acetone-d6): delta = 151.45 (C-2), 143.31 (C-8),134.51 (C-10), 131.77 (C-5), 129.36 (C-13), 129.32 (C-14), 128.25 (C-4), 127.74 (C-3), 127.49 (C-12), 124.90 (C-9), 124.03 (C-7), 122.28 (C-6), 122.21 (C-11). MS (ESI): m/z (%) = 214.1 [M + H]+ (100).HRMS (ESI): m/z [M + H]+ calcd for C13H9ClN: 214.0148; found:214.0149.

Statistics shows that Phenanthridin-6(5H)-one is playing an increasingly important role. we look forward to future research findings about 1015-89-0.

Reference:
Article; Sonawane, Manoj R.; Vavra, Jan; ?aman, David; Cisa?ova, Ivana; Teply, Filip; Synthesis; vol. 47; 22; (2015); p. 3479 – 3488;,
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Adding a certain compound to certain chemical reactions, such as: 711007-44-2, name is 2,3-Diaminobenzamide, belongs to amides-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 711007-44-2, Quality Control of 2,3-Diaminobenzamide

To a 100 ml three-neck flask was added 2,3-diaminobenzamide (3.2 g, 20 mmol), compound A (3.85 g, 22 mmol), sulfur powder (3.2 g, 100 mmol) was added, and stirred at 170 C. After 6 h, after cooling, 60 ml of methylene chloride was added and dissolved. The silicon gel was mixed and concentrated on a silica gel column. Chromatography on a silica gel column gave the desired product (C1) in a yield of 1.28 g (yield: 20%).

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, 2,3-Diaminobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong University Qilu Hospital; Tan Bingxu; (9 pag.)CN107556288; (2018); A;,
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