Category: 61903-11-5

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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., Recommanded Product: 61903-11-5

Bromopyrazole is mixed with K2CO3 and KI in 10 volumes of acetone at room temperature and N-acetylhomopiperazine was added over 1 hr. The reaction mixture was stirred until the reaction was complete. The mixture was filtered, removing the inorganics, washed with acetone and distilled to 2 volumes. The freebase was extracted into methyl THF/ EtOH and washed with NaCl and NaHCO3. The solvent was replaced with EtOH, a strength of the solution was determined, and 0.93 eq of HCl based on the available freebase was added to a mixture of acetone, ethanol and water. Careful monitoring of the pH yielded crystalline product in a 70% overall yield and the desired form 1.;To a cylindrical, jacketed 3 L reactor equipped with nitrogen inerting, agitator, condenser/distillation head, and temperature control, 5-bromo-pentanoic acid [5- (4-methoxy-phenyl)-lH-pyrazol-3-yl]amide (0.15 kg, 0.426 mol), potassium carbonate (0.059 kg, 0.426 mol), potassium iodide (0.071 kg, 0.426 mol), and acetone (1.18 kg, 1.5 L) were added (at 20 0C) to form a white mixture. The mixture was stirred (235 rpm) at 25-30 0C for a minimum of 15 min. N-acetylhomopiperazine (0.062 kg, 0.057 L, 0.434 mol) was added via addition funnel to the reactor over a minimum of 45 min., maintaining the temperature in the range of 25-30 0C. The addition funnel was rinsed with 0.05 L acetone. A white mixture persisted. The mixture was stirred (235 rpm) in the range of 25-30 0C for a minimum of 16 h, forming a white/yellow mixture. The reaction progress was monitored by HPLC and was considered complete when there was < 2% of the starting material (bromopyrazole) and < 2% of the iodopyrazole present. [00240] The reactor contents were cooled to 5-15 0C over a minimum of 15 min with agitation (295 rpm) to form a white/yellow mixture that was then stirred for a minimum of 1 h. To remove inorganics, the mixture was then filtered on a Buchner funnel with filter paper using house vacuum for 1.5 min. The cake was washed twice with acetone (total of 0.24 kg, 0.30 L) at 5-15 0C. The wash was combined with the mother liquor from the prior filtration and used to rinse the reactor. The filtrate was concentrated to a volume of approximately 0.45 L to form a clear solution.

The synthetic route of 61903-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; SIENA BIOTECH S.P.A.; WO2009/91832; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(1,4-Diazepan-1-yl)ethanone

A solution of lambda/-(7-chloro-2-methylpyrazolo[l,5-alpha]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol) and l-(l,4-diazepan-l-yl)ethanone (101 mg, 0.75 mmol) in DMF (1.0 mL) was stirred at 100 0C for 2h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (25-40% MeCN/H2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (87.7 mg, 78%). 1H NMR (DMSO-de) [1 :1 ratio of rotamers: delta: 10.93 (s, IH); 10.91 (s, IH)], 7.99 (d, J = 8.3 Hz, 2H), 7.62 (dd, 2H), [1 :1 ratio of rotamers: 7.13 (s, IH); 7.07 (s, IH)], [1 :1 ratio of rotamers: 6.19 (s, IH); 6.18 (s, IH)], [1 :1 ratio of rotamers: 4.37 (t, J = 5.6 Hz, 2H); 4.20 (t, J = 5.4 Hz, 2H)], [1 :1 ratio of rotamers: 4.03 (t, J = 5.6 Hz, 2H); 3.97 (t, J = 5.9 Hz, 2H)], 3.63 – 3.78 (m, 2H), [1 :1 ratio of rotamers: 3.58 (t, J = 5.9 Hz, 2H); 3.52 (t, J = 5.8 Hz, 2H)], 2.37 (s, 3H), [1 :1 ratio of rotamers: 2.03 – 2.11 (m, 2H); 1.94 (quin, J = 5.9 Hz, 2H)], [1 :1 ratio of rotamers: 2.02 (s, 3H); 1.89 (s, 3H)], 1.46 (s, 6H); ESI-MS: m/z 451.3 (M+H)+.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/123986; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 61903-11-5, 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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of the product of example Ii (160 mg), JV-acetylhomopiperazine (89 mg), DIPEA (370 muL) and HATU (192 mg) in dichloromethane (5 ml) was stirred at 400C for 1 h. The reaction mixture was diluted with ethyl acetate and washed with an aqueous HCl solution (0.2 M), water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [10/0 ? 8/2 (v/v)] as eluent.Yield: 230 mg; hFSHRago (CHO luc) EC50 = 5.2 nM

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-(1,4-Diazepan-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. ORGANON; WO2009/98283; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 61903-11-5, These common heterocyclic compound, 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, 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.

Lithium aluminum hydride (38.2 ml, 38.19 mmol) was added to 1-(1,4-diazepan-1-yl)ethanone (1.697 g, 11.93 mmol) in THF (59.7 ml) at 0 C. under nitrogen. The resulting solution was stirred at ambient temperature for 1 h and then at 60 C. for 1 h. The cooled reaction mixture was poured onto ice (500 mL), acidified with HCl (2M aqueous solution) and purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford 1-ethyl-1,4-diazepane (0.610 g, 40%) as a yellow liquid. This was used directly with no further purification. 1H NMR (399.9 MHz, CDCl3) delta 1.07 (3H, t), 1.74-1.80 (2H, m), 2.58 (2H, q), 2.64-2.70 (4H, m), 2.89-2.95 (4H, m).

Statistics shows that 1-(1,4-Diazepan-1-yl)ethanone is playing an increasingly important role. we look forward to future research findings about 61903-11-5.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

61903-11-5, 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 61903-11-5 as follows.

(e). 1-{4-[1-(4-Fluoro-phenyl)-8,9-dimethoxy-5,6-dihydro-imidazo[5,1-a]isoquinoline-3-carbonyl]-[1,41]diazepan-1-yl}-ethanone; hydrochloride salt A solution of the product of 50d (60 mg) in dioxane (1 ml) was treated with a solution of LiOH (20 mg) in water (0.3 ml). The mixture was stirred for 45 min and neutralized by addition of an aqueous HCl solution (0.5 N). The aqueous material was freeze-dried and diluted with DMF (1 ml). N-acetylhomopiperidine (30 mg), N-ethylmorpholine (30 ml) and TBTU (60 mg) were added. The reaction mixture was stirred for 4 h, poured in water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (dichloromethane/acetone as eluent). The product was dissolved in a mixture of acetone/ether (v:v, 1:1) and treated with one equivalent of a 0.4N HCl solution in ether. Yield: 10 mg. MS-ESI: [M+H]+=493.4; TLC Rf=0.50 (dichloromethane/acetone 1:1); NMR (DMSO-d6) delta 2.00 (m, 3, acetyl(rotamers)), 3.47 and 3.80 (2*s, 6, OCH3), 6.95 and 7.02 (2*s, 2, H7 and H10), 7.30 and 7.69 (2*m, F-Ar-H); 19F-NMR (DMSO-d6)-114.9; hFSHRago (CHO luc) EC50=315 nM.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 61903-11-5, and friends who are interested can also refer to it.

Reference:
Patent; N.V. Organon; US2010/324021; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

61903-11-5, 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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below.

iii) 5-(4-acetyl-[1,4]diazepan-1-yl)-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]amide (1.5 g, 4.26 mmol) was dissolved in DMF (15 mL), and sodium iodide (0.64 g, 4.26 mmol) was added followed by N-acetylhomopiperazine (0.56 mL, 4.26 mmol) and diisopropylethylamine (0.74 mL, 4.26 mmol). The reaction was stirred under N2 at 50 C. for 18 hrs. Upon reaction completion (as monitored by LCMS), the solvent was removed at reduced pressure and the resulting oily residue was dissolved in DCM (20 mL), washed with sat. Na2CO3 (2¡Á20 mL) and sat. NaCl (2¡Á20 mL), and dried over Na2SO4. Upon solvent removal, 1.7 g of crude product as a thick oil were obtained. The product was purified by SiO2 chromatography (10 g cartridge-flash SI II from IST) employing DCM and DCM:MeOH 9:1 to yield 0.92 g of pure product and 0.52 g of less pure product. A second purification of the impure fractions using a 5 g SiO2 cartridge was performed using the same eluent. Overall, 1.09 g of 5-(4-acetyl-[1,4]diazepan-1-yl)-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide were obtained (2.64 mmol, 62% yield) as a thick light yellow oil. MS (ES+): 414.26 (M+H)+.

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; SIENA BIOTECH S.P.A.; US2009/181953; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., 61903-11-5

A solution of N-(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)-N-phenylethenesulfonamide (0.100 g, 0.255 mmol), N-acetylhomopiperazine (0.073 g, 0.511 mmol) and N,N-diisopropylethylamine (0.176 mL, 1.022 mmol) in dichioromethane (5 mL) was stilTed at the room temperature for 18 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; methanol / dichloromethane = 3 % to 5 %) to give2-(4-acetyl- 1 ,4-diazepan- 1 -yl)-N-(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)- N-phenylethane-1-sulfonamide as white solid (0.032 g, 23.5 %).?H NMR (700 MHz, CDC13) oe 8.04 – 8.00 (m, 2 H), 7.45 (d, 2 H, J = 8.3 Hz), 7.36 -7.27 (m, 5 H), 6.91 (t, 1 H, J= 51.7 Hz), 4.96 (s, 2 H), 3.68 – 3.66 (m, 1 H), 3.64- 3.59(m, 1 H), 3.56 – 3.51 (m, 2 H), 3.36 – 3.33 (m, 1 H), 3.32 – 3.27 (m, 1 H), 3.13 – 3.07(m, 2 H), 2.79-2.66 (m, 4 H), 2.11 -2.09 (m, 3 H), 1.97 (m, 1 H), 1.88 – 1.87 (m, 1H);LRMS (ES) mlz 534.3 (M+1).

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; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics