Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 122734-32-1, name is tert-Butyl (2-(methylamino)ethyl)carbamate, 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 122734-32-1, Recommanded Product: tert-Butyl (2-(methylamino)ethyl)carbamate

To a solution of dichlorobenzyl-piperidin-4-one (Example 74, step (i), 4.8 g) and acetic acid (1 ml) in dichloromethane (100 ml) was added (2-methylamino-ethyl)-carbamic acid tert-butyl ester (3.26 g) and the mixture was stirred for 5 minutes before addition of sodium triacetoxyborohydride (7.9 g). The reaction mixture was stirred for 12 hours before addition of sodium bicarbonate solution. The mixture was stirred for 1/2 hour and then partitioned between water and dichloromethane. The organic layer was separated, dried (MgSO4) and solvent removed by evaporation. Purification by Biotage 40S eluding 10%MeOH/2% triethylamine/dichloromethane gave the title compound (1.7 g). MS: ESI 316/318 (+H-(CH3)4COCO) 1H NMR: (CDCl3): delta 1.44 (9H, s), 1.50-1.60 (4H, m), 1.65-1.72 (2H, m), 1.95 (2H, td), 2.23 (3H, s), 2.34 (1H, tt), 2.88 (2H, d), 3.14-3.20 (2H, m), 3.41 (2H, s), 4.95-5.01 (1H, m), 7.13-7.15 (1H, m), 7.37 (1H, d), 7.42 (1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(methylamino)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca, AB; US6903085; (2005); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127346-48-9, name is tert-Butyl (3-aminopropyl)carbamate hydrochloride, 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 127346-48-9, name: tert-Butyl (3-aminopropyl)carbamate hydrochloride

Step 1A. Synthesis of tert-butyl 3-(((3-((tert-butoxy)carbonylamino)propyl)methylamino)methyl)-4-fluorobenzoate Crude tert-butyl-4-fluoro-3(alpha-bromomethyl)benzoate (4.6 g., 16 mmol), prepared as described in (WO 95/18619, PCT/US95/00248), was dissolved in 100 mL THF, along with 3-tert-butoxycarbonylamino-1-propylamine hydrochloride (2.9 g., 16.6 mmol) and diisopropylethylamine added (4.6 g., 36 mmol). The solution was stirred overnight, diluted with 1N NaOH, and extracted with three portions of ether. The combined organics were washed with water and sat. NaCl, dried over MgSO4, and concentrated under vacuum to 5.7 g. of a yellow oil. This was purified by flash chromatography (CH2Cl2/EtOAc) to afford the product as a clear oil (2.04 g., ~35%). 1H-NMR (600 MHz, DMSO-d6): 7.99 (dd, J=2, 5.1 Hz, 1H), 7.78 (ddd, J=2.3, 2.8, 3.0 Hz, 1H), 7.22 (dd, J=8.8, 0.7, 1H), 6.73 (b, 1H), 3.68 (s, 2H), 2.94 (m, 2H), 2.15 (b, 1H), 1.51 (s, 9H), 1.49 (m, 2H), 1.33 (s, 9H); MS (ES): 765.4 [2M+H]+, 383.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-aminopropyl)carbamate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; US6569402; (2003); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, belongs to amides-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. Quality Control of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Compound 20 (10 g, 57 mmol)Soluble in 250mL of dry dichloromethane,Nitrogen bubbling,Dess-Martin oxidant (DMP, 26.6 g) was added in portions at 0 C.Add the room temperature reaction,TLC (PE/EA = 1/1) monitors the progress of the reaction.Post-processing,Add 500 mL of saturated sodium bicarbonate solution,500mL saturated aqueous sodium thiosulfate solution andStir in 800 mL of dichloromethane for 30 min.Layered, the organic layer is saturated with sodium bicarbonate,Saturated with sodium chloride,Dry over anhydrous sodium sulfate, filter,Concentration under reduced pressure gave a white oil, 8.65 g.

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Bai Li Pharmaceutical Co., Ltd.; Zhu Yi; Li Jie; Wan Weili; Zhuo Shi; Li Gangrui; (28 pag.)CN109106951; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 147751-16-4, 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. 147751-16-4 name is tert-Butyl methylsulfonylcarbamate, 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 solution of terf-butyl methylsulfonylcarbamate (900 mg, 4.62 mmol), K2CO3 (1 .3 g, 9.63 mmol) in DMF (60 mL) was added 2-(chloromethyl)-6-(1 -(phenylsulfonyl)-l H-indol- 3-yl)benzo[d]oxazole (Intermediate 79, 1 .49 g, 3.52 mmol). The mixture was stirred at 50 C for 9 hrs. The reaction mixture was filtered. The filtrate was diluted with water (60 mL) and extracted with EtOAc (60 mLx3). The combined organic layer was washed with water (60 mLx3), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and purified by silica gel chromatography (petroleum ether/ EtOAc =6/1 – 3/1 ) to afford 1 .25 g (61 %) of the title compound as a yellow solid. LC-MS for C28H27N3O7S2+H+ [M+H]+ : calcd. 582.1 ; found: 582.7. 1H NMR (400 MHz, DMSO-afe) delta [ppm]:8.22 (s, 1 H), 8.13 (d, J = 1 .1 Hz, 1 H), 8.11 (s, 1 H), 8.09 (d, J = 1 .3 Hz, 1 H), 8.05 (d, J = 8.3 Hz, 1 H), 7.89 (d, J = 7.9 Hz, 1 H), 7.85 (d, J = 8.3 Hz, 1 H), 7.76 (dd, J = 8.3, 1 .5 Hz, 1 H), 7.73 – 7.68 (m, 1 H), 7.61 (t, J = 7.7 Hz, 2H), 7.47 – 7.42 (m, 1 H), 7.39 – 7.34 (m, 1 H), 5.17 (s, 2H), 3.57 (s, 3H), 1 .43 (s, 9H).

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

Reference:
Patent; ITEOS THERAPEUTICS; CAUWENBERGHS, Sandra; CROSIGNANI, Stefano; DRIESSENS, Gregory; DEROOSE, Frederik; (271 pag.)WO2015/140717; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 141449-85-6, 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. 141449-85-6 name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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.

A 40-mL vial was charged with 4-chlorobenzaldehyde (1.13 g, 8.04 mmol, 1.00 equiv), 1,2-dichloroethane (20 mL), tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate (1.69 g, 7.96 mmol, 0.99 equiv) and sodium triacetoxyborohydride (5.09 g, 24.0 mmol, 2.99 equiv). The resulting solution was stirred overnight at room temperature and quenched by water (10 mL). The mixture was extracted with DCM (3 x 30 mL) and the organic layers were combined, washed with water (3 x 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 2.15 g (79% yield) of tert-butyl 5-(4-chlorobenzyl)hexahydropyrrolo[3,4-c]pyrrole-2(lH)- carboxylate as an off-white solid. LCMS (ESI, m/z): 337 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; JONES, Todd K.; DUNCAN, Katharine K.; WEBER, Olivia D.; CISAR, Justin S.; MERIT, Jeffrey E.; (184 pag.)WO2017/87858; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 198989-07-0, A common heterocyclic compound, 198989-07-0, name is tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, molecular formula is C10H18N2O2, 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 2.4: To a solution of 1?-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1 ,3?-indoline]- 6?-carboxylic acid (0.25 g, 0.62 mmol, 1 eq) in DMF (5 mL), the TBTU (0.24 g, 0.747 mmol, 1.2 eq), NMM (0.126 g, 1.25 mmoL, 2 eq) and 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.123 g, 0.623 mmol, 1 eq) were added at RT. RM was then stirred at RT for 16 h. After completion of reaction,reaction mixture was quenched with ice water (40 mL) and a solid was precipitated out. The solid was filtered off and re-dissolved in EtOAc (50 mL). The EtOAc solution of the desired compound was washed with water (2 x 40 mL), brine (40 mL), dried over Na2SO4, filtered and evaporated under reduced pressure to get the crude product. The crude product was triturated with Et20-hexane (3 x) to afford tert-butyl 5-(1 (5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1 ,3-indolinj-6?-ylcarbonyl)-2,5-diazabicycle-[2.2.1]heptane-2-carboxylate (0.35 g, 96.9%) as white solid.

The synthetic route of 198989-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; HESSLINGER, Christian; DOODEMAN, Robin; (0 pag.)WO2016/8593; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 67442-07-3, 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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

iPrMgCl*LiCl (Turbo Grignard, 1.3 mol/L in tetrahydrofuran, 25.6 mL) is added dropwise to a flask charged with a stir bar, 2-iodo-5-bromo-pyridine (9.00 g), and tetrahydrofuran (180 mL) and chilled to -30¡ã C. The mixture is stirred in the cooling bath for 1 h. 2-Chloro-N-methoxy-N-methylacetamide (4.58 g) dissolved in tetrahydrofuran (20 mL) is added dropwise over 5 min. The mixture is stirred for 30 min and then quenched by the addition of aqueous 1 M HCl solution. The mixture is concentrated, and the aqueous residue is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1?1:1) to give the title compound. Mass spectrum (ESI+): m/z=234/236/238 (Br+Cl) [M+H]+.

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

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; WAGNER, Holger; PETERS, Stefan; (43 pag.)US2018/148411; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 56619-93-3, The chemical industry reduces the impact on the environment during synthesis 56619-93-3, name is N-(3-Methoxyphenyl)pivalamide, I believe this compound will play a more active role in future production and life.

Synthesis of N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (1b) Under the argon atmosphere, n-butyllithium (nBuLi) (2.6 M in THF, 111 mL, 289 mmol, commercial product) was slowly dropped at 0C into a tetrahydrofuran (THF) (400 mL, dehydrated, commercial product) solution of the compound 1a (30.0 g, 145 mmol). After the mixture was stirred at 0C for 2 hours, ethylene oxide (1.3 M ether solution, 175 mL, 228 mmol, commercial product) was slowly added to the mixture and stirred at 0C for 1 hour. The temperature was raised to room temperature, and then the mixture was further stirred for 2 hours. The mixture was concentrated under reduced pressure, to which a saturated ammonium chloride aqueous solution (sat. NH4Cl aq.) was added. Subsequently, the mixture was extracted with ethyl acetate (EtOAc) (100 mL * 4). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized with ethyl acetate (EtOAc), and thus N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (compound 1b) (28.1 g, 112 mmol, 77.1%) was obtained as a colorless solid. TLC Rf= 0.40 (n-hexane/EtOAc = 3/1)

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-(3-Methoxyphenyl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyoto University; National University Corporation Tokyo Medical and Dental University; Kinopharma, Inc.; HAGIWARA, Masatoshi; ONOGI, Hiroshi; KII, Isao; HOSOYA, Takamitsu; SUMIDA, Yuto; EP2881397; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1012884-46-6, name is 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one, molecular formula is C17H12ClNO2, 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. COA of Formula: C17H12ClNO2

Example 1; Preparation of trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (IV); following Scheme II A. Mixture of trans-(IV) and cis-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (V); Under N2 atmosphere, iodine (4.95 g, 18 mmol) was added to a stirred suspension of magnesium (1.75 gram, 71.87 mmol) in toluene (175 mL). Over a period of 20 minutes, a solution of 11-chloro-2,3-dihydro-2-methyl-1H-dibenz[2,3;6,7]oxepino[4,5-c]pyrrol-1-one (III) (25 gram, 84 mmol; see Vader et al., above) in methanol (175 mL) was added. The reaction mixture was stirred for 35 minutes. Then, over a period of 2 hours, 3 portions of magnesium (1 g, 41.06 mmol) followed by one larger portion of magnesium (2 g, 82.12 mmol) were added. Water (600 mL) and 36% hydrochloric acid (65 mL) were added keeping the temperature below 40 C. Toluene (50 mL) was added, the layers were separated, and the water layer was extracted with toluene (2¡Á100 mL). The combined toluene layers were washed with water (200 mL), dried over magnesium sulfate, filtered and evaporated. This gave a mixture of trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino [4,5-c]-pyrrol-1-one (IV) and cis-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (V) (25.5 g, 100%) in the ratio (IV):(V)=1:4 as determined by 1H-NMR and GC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1012884-46-6, its application will become more common.

Reference:
Patent; Organon Ireland Ltd.; Pfizer Inc.; US2006/229352; (2006); 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. 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H19NO3

To a solution of PPh3 (240 mg, 0.91 mmol) in anhydrous THF (4 mL) was added DIAD (185 mg, 0.91 mmol) by syringe at 05 C, followed a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (185 mg, 0.91 mmol) in anhydrous THF (2 mL). The resulting mixture was poured into a solution of compound 308-5 (118 mg, 0.30 mmol) in dry THF (2 mL) at ambient temperature and stirred for 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (dichloromethane/ethyl acetate: 3/1) to afford the title compound 309-15 as a yellow solid (300 mg).

According to the analysis of related databases, 153248-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics