Category: amides-buliding-blocks

Some common heterocyclic compound, 27466-83-7, name is 4-Bromo-N-methylbenzamide, molecular formula is C8H8BrNO, 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. Computed Properties of C8H8BrNO

General procedure: N-Propylbenzamide (A1) (40.8 mg, 0.25 mmol, 1.0 equiv), Oxone(307.8 mg, 0.50 mmol, 2.0 equiv), KBr (8.9 mg, 0.075 mmol, 0.3equiv), H2O (198.2 mg, 44 equiv, 0.2 mL) and CH2Cl2 (1.5 mL) wereadded to a 15 mL sealed tube containing a magnetic stir bar. The reaction mixture was stirred at room temperature for 7 hours under irradiation with an 8 W white LED. After completion of the reaction, saturated Na2SO3 (5.0 mL) was added and the mixture was extracted with CH2Cl2 (3 ¡Á 10 mL). The combined organics were washed with brine(10 mL), dried over Mg2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/PE,1:6) to afford N-propionylbenzamide (B1). 3b White solid; yield: 37.7 mg (85%); mp 93-94 C (Lit. 3b 93-94 C).1 H NMR (400 MHz, CDCl 3 ): delta = 8.54 (br s, 1 H), 7.84 (d, J = 7.2 Hz, 2 H),7.61 (t, J = 7.6 Hz, 1 H), 7.51 (t, J = 8.0 Hz, 2 H), 3.04 (q, J = 7.2 Hz, 2 H),1.23 (t, J = 7.6 Hz, 3 H).13 C NMR (100 MHz, CDCl 3 ): delta = 177.8, 166.0, 133.3, 133.0, 129.1,128.0, 31.5, 8.4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27466-83-7, its application will become more common.

Reference:
Article; Mei, Chong; Hu, Yixin; Lu, Wenjun; Synthesis; vol. 50; 15; (2018); p. 2999 – 3005;,
Amide – Wikipedia,
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Related Products of 2895-21-8, 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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 7-iodo-3-[3-(methyloxy)phenyl]pyrrolo[1 ,2-a]pyrazin-1 (2H)-one (370 mg, P2) in dry DMF (10 ml_), NaH (42.4 mg, 60% w/w) was added at 0 0C under nitrogen atmosphere. The mixture was stirred for 30 min at room temperature, that it was cooled down to 0 0C and NaI (227 mg) and 2-chloro-N-(1-methylethyl)acetamide (144 mg) were added and the mixture was stirred at 65 0C over night. Chilly water was added to the reaction mixture and the product was extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and the solvent was evaporated under vacuum. The crude was purified by flash column chromatography on silica gel (eluent AcOEt:Cy with a gradient from 20% to 50% of AcOEt) to give the title compound (215 mg).MS (m/z): 466 [MH]+

The chemical industry reduces the impact on the environment during synthesis N-Isopropyl-2-chloroacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/130231; (2009); A1;,
Amide – Wikipedia,
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Reference of 198211-38-0, 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. 198211-38-0, name is tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

Example 3; Synthesis of 6-amino-3-azabicyclo[3.1.0]hexane-3-N-(4-fluorophenyl)carboxamide (pTSA salt)Step a: Synthesis of tert-butyl (3-{[(4-fluorophenyl)amino]carbonyl}-3-azabicyclo[3.1.0]hex-6-yl)carbamateTo a solution of tert-butyl 3-azabicyclo[3.1.0]hex-6-ylcarbamate (0.500 g, 2.50 mmol) in dichloromethane (10.0 mL) at 0 C., was added dropwise a solution of 4-fluorophenyl isocyanate (0.34 mL, 3.0 mmol) in dichloromethane (5.0 mL) and stirred at 0 C. for about 3 hours. The reaction mixture was partitioned between water (10.0 mL) and dichloromethane (20.0 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to yield the title product, which was used directly in the next step.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sattigeri, Jitendra A.; Andappan, Murugaiah M.S.; Kishore, Kaushal; Sethi, Sachin; Kandalkar, Sachin Ramesh; Pal, Chanchal Kumar; Mahajan, Dipak C.; Ahmed, Shahadat; Parkale, Santhosh Sadashiv; Srinivasan, T.; Sharma, Lalima; Bansal, Vinay S.; Chugh, Anita; Davis, Joseph Alexanand; US2008/300251; (2008); A1;,
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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. 337463-88-4, name is 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, A new synthetic method of this compound is introduced below., Safety of 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

f) 6-Bromo-7-chloro-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (20 g, 87.7 mmole) was dissolved in DMF (175 mL) and cooled in an ice bath. Chlorine gas was then slowly bubbled in for 45 minutes, and then the saturated solution was stirred in the ice bath for 2 hours. The mixture was purged with nitrogen and slowly added with stirring to 1 L of ice water which contained 100 g of Na2SO3, making sure to keep the temperature <15 C. After stirring 30 minutes the product was filtered, washed thoroughly with water and dried to afford (22.5 g, 98%) of a white solid.1H NMR (400 MHz, DMSO-d6): 4.76 (2H, s,), 7.78 (1H, s),11.71 (1H, s). 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:
Patent; Glaxo Group Limited; US2008/194547; (2008); A1;,
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Application of 630-22-8, These common heterocyclic compound, 630-22-8, name is 2,2-Dimethylpropanethioamide, 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.

Intermediate 38: 2-Propen-1-yl {5-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate; To a solution of 2-propen-1-yl {5-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate (35 g, 100.3 mmol in DMA, 500 mL), NBS (17.8 g, 100.3 mmol) was added. The reaction mixture was stirred at rt for 1 h. Then 2,2-dimethylpropanethioamide (13 g, 111 mmol) was added at 0 C. The mixture was stirred at 80 C. for 2 h. The mixture was poured into water and extracted with EtOAc (1 L¡Á3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (DCM:petroleum ether 2:1) to afford the title compound (36 g, 80.5% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.24-8.31 (m, 2H), 7.09-7.18 (m, 2H), 7.01 (d, J=5.5 Hz, 1H), 6.92-6.98 (br, 1H), 5.87-5.97 (m, 1H), 5.31-5.37 (m, 1H), 5.24-5.28 (m, 1H), 4.61-4.65 (m, 2H), 1.46 (s, 9H).

The synthetic route of 630-22-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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Application of 121492-06-6, 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a cooled (0 C) solution of NMethylNbocethylendiamine (05 mL, 279 mmol) and NaCNBH3 (140 mg, 223 mmol) in MeOH (10 mL) and acetic acid (05 mL) was added a solution of 2,4,6trimethoxyhenzaldehyde (0 547 mg 279 mmol) in EtOH (10 mL). The mixture was stirrcd at RI for 2 h, acidificd with 2 M HCI (1 mL) and neutralized withsaturated aqueous Na2CO3 (50 mL). Evaporation of all volatiles, DCM extraction of the resulting aqueous slurry and concentration of the organic fractions yielded N MethylNbocN? tmobethy1endiamine (5a) as a crude oil which was purified by RPHPLC.Yield 593 ing (L52 mmol)MS. rn z 377 35 [M+Na], (calculated = 377 14).

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-Boc-(2-Aminoethyl)-N-methylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASCENDIS PHARMA RELAXIN DIVISION A/S; SPROG?E, Kennett; CLEEMANN, Felix; RAU, Harald; HASSEPASS, Nicole; WEGGE, Thomas; ZETTLER, Joachim; BERNHARD, Ana; WO2015/67791; (2015); A1;,
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Reference of 108468-00-4, 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. {(S)-l-[4-(tert-Butoxycarbonylamino-methyl)-benzylcarbamoyl]-2-phenyl-ethyl}- carbamic acid benzyl ester (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 2,5-dioxo-pyrrolidin-l-yl ester (4.25g, 10.72mmol) was dissolved in CH2CI2 (100 mL). This solution was cooled to 0C. l-(N-Boc- Aminomethyl)-4-(aminomethyl)benzene (2.79g, 11.79mmol) was added followed by triethylamine (3.25g, 32.16mmol). After 18 hrs at 0C to room temperature reaction mixture was diluted with chloroform (100 mL) and washed with NaHC03 (1×30 mL), water (1×30 mL), brine (1×30 mL), dried (Na2S04) evaporated in vacuo giving a yellow oil. The residue was triturated with Pet. Ether (60-80C) and EtOAc to give a white solid identified as {(S)-l-[4-(tert- butoxycarbonylamino-methyl)-benzylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (3.88g, 7.49mmol, 70%). [M+H]+ = 518.28, 540.32 (M+Na).

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-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KALVISTA PHARMACEUTICALS LIMITED; EVANS, David Michael; DAVIE, Rebecca Louise; EDWARDS, Hannah Joy; ROOKER, David Philip; WO2013/5045; (2013); A1;,
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Electric Literature of 711007-44-2, These common heterocyclic compound, 711007-44-2, name is 2,3-Diaminobenzamide, 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.

Step-4: To a solution of 2-((benzyloxy)carbonyl)-3-methyl-l,2,3,4- tetrahydroisoquinoline-3-carboxylic acid (620 mg, 1.91 mmol) in anhydrous DMF (5 ml) was added EDCHCl (1.098 mg, 5.73 mmol), HOAt (390 mg, 2.87 mmol) and triethylamine (0.4 ml, 2.87 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3- diaminobenzamide (346 mg, 2.29 mmol) was added and heated to 550C for 3 days. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum and purified by preparative TLC using ethyl acetate as eluent to afford benzyl 3-((2-amino-3-carbamoylphenyl)carbamoyl)-3-methyl-3,4-dihydroisoquinoline- 2(lH)-carboxylate. MS (ES+): m/z 481.2 [M+ Na]+

The synthetic route of 711007-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; LIM, Dong, Sung; SMITH, David, E.; WO2011/2520; (2011); A2;,
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Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 22726-00-7, name is 3-Bromobenzamide, molecular formula is C7H6BrNO, 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. HPLC of Formula: C7H6BrNO

A mixture of 3-bromobenzamide (3 g, 15.1 mmol), [3-(hydroxymethyl)- phenyl]boronic acid (3 g, 19.6 mmol), PdCl2(PPh3)2 (0.46 g, 0.66 mmol), and potassium carbonate (3.6 g, 26.2 mmol) in Toluene/MeOH (10:1, 40 mL) was stirred at 80 C for 18 h. The resulting black mixture was cooled to room temperature, filtered through celite, and poured into a EtO Ac/brine mixture. The two layers were separated and the aqueous was extracted with EtOAc (3x). The organics were combined, dried over sodium sulfate, filtered, and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with a mixture of EtOAc/Hexane to give 3′-(hydroxymethyl)biphenyl-3-carboxamide as a solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22726-00-7, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2006/14918; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16695-22-0, 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. 16695-22-0, name is (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate), This compound has unique chemical properties. The synthetic route is as follows.

9 was obtained from myricetin (509 mg, 1.6 mmol), K2CO3 (276 mg, 2.0 mmol), N,O,O’-Tri(toluene-4-sulfonyl)diethanolamine (454 mg, 0.8 mmol) and DMF (30 mL), according to the general procedure, as a light yellow amorphous powder (402 mg, yield: 45%); UV (MeOH) lambdamax(log epsilon) 364 (2.56) nm; IR (K Br)numax: 3397, 2923, 1656, 1160, 1048 cm-1. 1H NMR (DMSO-d6, 400 MHz): delta 12.39 (1H, br s, 5-OH), 7.63 (2H, d, J = 8.0 Hz, H-6″, 10″), 7.47 (1H, s, H-2′), 7.38 (2H, d, J = 8.0 Hz, H-7″, 9″), 7.31 (1H, s, H-6′), 6.43 (1H, s, H-8), 6.20 (1H, s, H-6), 4.41 (2H, br s, H-1″), 4.23 (2H, br s, H-2″), 3.44 (4H, br s, H-3″, 4″), 2.36 (3H, s, H-11″); 13C NMR (DMSO-d6, 100 MHz): delta 176.1 (C-4), 164.5 (C-7), 160.7 (C-5), 156.2 (C-9), 152.5 (C-3′), 150.6 (C-5′), 145.2 (C-2), 143.3 (C-8″), 140.9 (C-5″), 136.9 (C-4′), 135.1 (C-3), 129.9 (C-7″, 9″), 126.9 (C-6″, 10″), 126.1 (C-1′), 111.9 (C-6′), 110.2 (C-2′), 103.0 (C-10), 98.4 (C-6), 93.5 (C-8), 73.2 (C-1″), 72.7 (C-4″), 52.2 (C-3″), 51.9 (C-2″), 20.9 (C-11″); HRESIMS m/z 542.1113 [M-H2O+H]+ (calcd for [C26H24NO10S]+, 542.1115).

The chemical industry reduces the impact on the environment during synthesis (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate). I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Jia; Wu, Yuechan; Zou, Jianwei; Gao, Kun; Bioorganic and Medicinal Chemistry; vol. 24; 7; (2016); p. 1488 – 1494;,
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