Tag: M.W=200-300

Reference of 956434-30-3, These common heterocyclic compound, 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, 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 1) To a solution of (2S)-butan-2-ol (0.32 mL) in toluene (8 mL) was added sodium hydride (0.28 g), and the resulting mixture was stirred at 70C for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (1.0 g), BINAP (0.066 g), Pd2(dba)3 (0.048 g) and toluene (8 mL) was added, and the resulting mixture was stirred at 100C for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?40% ethyl acetate/hexane) to give tert-butyl 8-{[(1S)-1-methylpropyl]oxy}-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.73 g, 65%) as a white powder. 1H-NMR(CDCl3):delta0.94(3H,t,J=7.4Hz), 1.27(3H,d,J=6.3Hz), 1.42(9H,s), 1.63-1.75(2H,m), 3.76-3.86(2H,m), 4.21(2H,brs), 4.34-4.43(2H,m), 5.10(1H,brs), 6.39(1H,d,J=8.1Hz), 7.38-7.47(1H,m)

Statistics shows that tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate is playing an increasingly important role. we look forward to future research findings about 956434-30-3.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2213675; (2010); A1;,
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Reference of 142733-64-0,Some common heterocyclic compound, 142733-64-0, name is tert-Butyl (cis-3-(hydroxymethyl)cyclobutyl)carbamate, molecular formula is C10H19NO3, 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.

To a solution of II-29-1 (200 mg, 1.0 mmol) and Et3N (202 mg, 2.0 mmol) in CH2C12(10 mL) was added MsCl (172 mg, 1.5 mmol) at 0 C. The reaction mixture was stirred at room temperature overnight before water was added to the reaction. The solution mixture was extracted with CH2C123 times. The organic layer was washed with brine and dried over Na2S04. The solution was filtered and concentrated to give II-29-2 as a white solid (250 mg, yield: 90%).

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 (cis-3-(hydroxymethyl)cyclobutyl)carbamate, its application will become more common.

Reference:
Patent; KURA ONCOLOGY, INC.; BURROWS, Francis; KESSLER, Linda V.; LI, Liansheng; REN, Pingda; WANG, Yi; WU, Tao; ZHANG, Jingchuan; (355 pag.)WO2018/175746; (2018); 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. 919475-15-3, name is 2-(4-(Benzyloxy)phenyl)-N,N-dimethylacetamide, A new synthetic method of this compound is introduced below., SDS of cas: 919475-15-3

A solution of 2N lithium diisopropylamide (LDA) (48.25 mL, 96.5 mmol) was cooled to -78¡ã C. and diluted with 25 mL of tetrahydrofuran (THF). To this was added dropwise, a solution of 2-(4-Benzyloxy-phenyl)-N,N-dimethyl-acetamide (20 g, 74.3 mmol) in 250 mL of THF. The mixture was warmed to 0¡ã C., then cooled back to -78¡ã C. A solution of 1,4-cyclohexanedione mono-ethylene ketal (14.1 g) in 350 mL of THF was added. The solution was allowed to warm to -20¡ã C. Highthroughput liquid chromatography (HPLC) assay still showed starting material. Another 1 g of ketal was added and the solution was warmed to 0¡ã C. for 2 hour. The reaction was quenched with a mixture of 25 g NH4Cl in 200 mL of water. EtOAc was added and the layers separated. The organic layer was dried with MgSO4, filtered and concentrated. Column chromatography (50percent EtOAc/hexanes) gave 30.3 g, 96percent yield of a solid

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; Wyeth; US2007/15828; (2007); 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. 121496-39-7, name is tert-Butyl benzyl(2-hydroxyethyl)carbamate, A new synthetic method of this compound is introduced below., SDS of cas: 121496-39-7

Under nitrogen atmosphere, to an ice-cooled solution of 4-iodophenol (15.40 g), triphenylphosphine (22.03 g), and tert-butyl benzyl (2-hydroxyethyl) carbamate (21.05 g) in tetrahydrofuran (123 ml) was added diethyl azodicarboxylate (14.58 g) in tetrahydrofuran (31 ml) for 25 minutes, and the mixture was stirred at room temperature for 2 hours. After being concentrated, the mixture was treated with HEXANE/ETHYL acetate (5/1, 180 ml). The precipitate formed was filtered off, the filtrate was concentrated, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give tert-butyl benzyl [2- (4- iodophenoxy) ethyl] carbamate (7.17 G) as a colorless oil. NMR (CDC13, B) : 1.45 (9H, s), 3.58 (2H, br s), 4.07 (2H, br s), 4.55 (2H, s), 6.62 (2H, d, J=8Hz), 7.10- 7.40 (5H, m), 7.53 (2H, d, J=8HZ) (+) ESI-MS (m/z): 476 (M+Na) +

The synthetic route of 121496-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD; WO2004/45610; (2004); A1;,
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Related Products of 21440-97-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 21440-97-1 as follows.

Example 6 Preparation of 6-bromo-4,4-dimethyl-benzoxazine-2-one Lithium Salt Similarly, 6-bromo-4,4-dimethyl-benzoxazine-2-one (2.55 g) was reacted with lithium tert-butoxide (10 mL of 1M solution in THF). After evaporation a brownish solid was obtained (3.35 g; quant. yield) that was soluble in dimethyl pyrimidone (DMPU) without heating. 1H NMR (DMSO-d6) did not show a peak corresponding to a N-H group.

According to the analysis of related databases, 21440-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2005/250766; (2005); A1;,
Amide – Wikipedia,
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Related Products of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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.

To a stirred solution of 2-amino-5-bromobenzamide (7.8 g, 0.036 mol), 4-methyl pentanoic acid (8.41 g, 0.O72mmol), and TBTU (17.46 g, 0.054 mol) in DMF (100 mL) was added DIPEA (25 mL, 0.154 mol) and the reaction mixture was stirred at room temperature for 14 h. The reaction mixture was diluted with water (100 mL)and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with aq. sodium bicarbonate solution (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, and the volatiles were evaporated to dryness. The residue was purified by silica gel column chromatography using a gradient of 40% ethyl acetate in hexanes and the required fractions were collectedand volatiles were evaporated to give 5-bromo-2-(4-methylpentanamido)benzamide (7.0 g, 0.022 mol, 55% yield) as a brown solid. LCMS (ESI) m/e 313.0 (bromo pattern) [(M+H), calcd for C13H18BrN2O2, 313.05]; LC/MS retention time (LC/MS Method = Column – YMC PACK TMS (3X5Omm), 3.0 rim; Mphase A: 2%MeCN98%H20 – 10mM NH4OAc; Mphase B : 98%ACN – 2%H20 -10 mM NH4OAC;Flow: 1.2 mL/min)): ti = 2.12 mm.

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-5-bromobenzamide, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); 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. 131818-17-2, name is tert-Butyl (4-bromophenyl)carbamate, A new synthetic method of this compound is introduced below., Product Details of 131818-17-2

b) tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).

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; Abbott Laboratories; US6921763; (2005); B2;,
Amide – Wikipedia,
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Reference of 6971-74-0, These common heterocyclic compound, 6971-74-0, name is N-Tosylbenzamide, 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.

General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2¡¤H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. An anhydrous toluene (1.0 mL) solution of ethyl diazoacetate 4a (30 muL, 0.30 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane=1:2) to give isoindolinone 3i in 80% yield.

The synthetic route of 6971-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
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Related Products of 24036-52-0, A common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, molecular formula is C8H6BrNO2, 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.

General procedure: To a solution of 5 (350mg, 1.54mmol) in 20mL THF was added phenylboronic acid (3.28mmol), copper acetate (420mg, 2.31mmol), Et3N (0.5mL, 4.62mmol) and 4A molecular sieve (50mg). The solution was stirred at 60C for 6h. After the completion of the reaction (monitored by TLC), the reaction solution was concentrated, and added with 20mL water. The reaction was filtered to remove solids and extracted with EtOAc, the organic layer was collected and washed with saturated salt solution for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford target product.

The synthetic route of 24036-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Guoyi; Pu, Chunlan; Lan, Suke; Zhong, Xinxin; Zhou, Meng; Hou, Xueyan; Yang, Jie; Shan, Huifang; Zhao, Lifeng; Li, Rui; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 667 – 686;,
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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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., Recommanded Product: 138-41-0

General procedure: To a solution of the carboxylic acids 33-36 (0.45 mmol) indimethylformamide (3 mL), an excess of EDCI (0.54 mmol) andhydroxybenzotriazole monohydrate (0.54 mmol), and a catalytic amount ofdimethylaminopyridine (0.02 mmol) were added. The mixture was stirred at roomtemperature for 2 h, then 5-(4-(aminomethyl)piperidin-1-yl)-2-(furan-2-yl)thiazolo[5,4-d]pyrimidin-7-amine(32) (0.49 mmol) was added. After stirring at room temperature for 3 h,20 mL of H2O were added to precipitate a solid which was filtered,washed with water and purified by column chromatography. N-((1-(7-Amino-2-(furan-2-yl)thiazolo[5,4-d]pyrimidin-5-yl)piperidin-4-yl)methyl)-4-sulfamoylbenzamide(8) Yield 85%. Mp: 166-168 C (column chromatography, eluting system ethylacetate/cyclohexane/methanol 7/2/1). 1H NMR (DMSO-d6): delta 8.71(t, 1H, NHCO, J=5.3 Hz), 8.00(d, 2H, J=8.4 Hz), 7.93-7.83(m, 3H), 7.48 (s, 2H, NH2), 7.24 (s, 2H, NH2), 7.05 (d,1H, J=3.2 Hz), 6.73-6.72 (m,1H), 4.68 (d, 2H, J=12.7 Hz),3.21-3.18 (m, 2H), 2.83 (t, 2H, J=12.0Hz), 1.86 (br s, 1H), 1.75 (d, 2H, J=11.8Hz), 1.14-1.11 (m, 2H). 13C NMR (DMSO-d6): delta 165.82,165.14, 159.21, 157.23, 148.62, 146.61, 145.80, 138.01, 128.34, 126.06, 124.69,113.20, 110.08, 45.35, 44.18, 36.55, 30.08. Anal. calcd. for (C22H23N7O4S2):C, 51.45%; H, 4.51%; N, 19.09%. Anal. found: C, 51.76%; H, 4.85%; N, 19.33%.

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; Catarzi, Daniela; Colotta, Vittoria; Espindola Gelsleichter, Nicolly; Guilbaud, Audrey; Lopes Rangel Fietto, Juliana; Pasquini, Silvia; Pelletier, Julie; Sevigny, Jean; Sarlandie, Marine; Varani, Katia; Varano, Flavia; Vincenzi, Fabrizio; Bioorganic and medicinal chemistry letters; (2020);,
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