Category: 79463-77-7

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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate, A new synthetic method of this compound is introduced below., 79463-77-7

6.1 To a solution of 4-(2-keto-1-benzimidazolinyl)piperidine (1.3 g; 5.98 mmol) in acetonitrile was added diphenyl N-cyanocarbonimidate (1.56 g; 6.55 mmol; 1.1 equiv). The reaction mixture was stirred at 60 C. for 48 h under nitrogen atmosphere and then concentrated under reduced pressure. The crude product was suspended in ethyl acetate (50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL) and stirred overnight at room temperature. The solid was collected by filtration and dried to give N-cyano-4-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboximidic acid phenyl ester (1.85 g; 85%) as a white 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; Icagen, Inc.; US2003/171360; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

79463-77-7,Some common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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 solution of (R)-3-tert-butoxycarbonylaminopipiridine (154.0 g, 0.769 mol) in iPrOH (3.0 L) was added diphenyl cyanocarbonimidate (183.2 g, 0.769 mol). The mixture was stirred at room temperature for 2.5 h. To the reaction mixture was added glycine ethyl ester¡¤hydrochloride (536.7 g, 3.85 mol) at 0 C, and the mixture was stirred at 80 C for 6 h. After cooling to room temperature, the reaction mixture was diluted with AcOEt (1.4 L) and the precipitate was removed by filtration through a Celite pad. The filtrate was concentrated in vacuo, and the residue was diluted with 5% sodium carbonate solution and extracted with CHCl3 three times. The combined organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica-gel column chromatography to give 7 (249.2 g, yield 92%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) delta 5.68 (br s, 1H), 4.66 (br s, 1H), 4.28-4.19 (m, 4H), 3.81-3.34 (m, 5H), 2.05-1.51 (m, 4H), 1.45 (s, 9H), 1.30 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 169.6, 160.0, 155.5, 117.1, 80.1, 61.8, 51.2, 47.3, 45.4, 44.6, 29.8, 28.3, 22.8, 14.1; HRMS (ESI) [M+H]+ calcd for C16H28N5O4 354.2136, found 354.2128; IR (ATR): 1743, 1685, 1575, 1531, 1440, 1390, 1365, 1309, 1243, 1197, 1162, 1051, 1031, 1018 cm-1.

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

Reference:
Article; Ikuma, Yohei; Nakahira, Hiroyuki; Tetrahedron; vol. 67; 49; (2011); p. 9509 – 9517;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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. 79463-77-7

To a stirred suspension of rac-allyl [3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazol-4-yl]carbamate (intermediate 7), 50.0 g (0.159 mol) in 2-propanol (860 mL) was added diphenyl N- cyanocarbonimidate, 38.0 g (0.159 mol). The reaction mixture was heated to reflux at which point the suspension dissolved into solution after a further 10 minutes at reflux a white precipitate formed. The reaction mixture was stirred at reflux for a further 1 hour before allowing to slowly cool to room temperature overnight. The precipitate was filtered, washing with diethyl ether (2 x 250 mL) and the resulting white solid was allowed to dry to yield rac-phenyl 4-{ [(allyloxy)carbonyl]amino}-N-cyano- 3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazole-l-carboximidate as a white solid, 48.6 g (67 %). NMR (400 MHz, DMSO-d6): delta [ppm] = 4.13 (apparent d, IH), 4.47 (m, 3H), 5.14 (dd, 2H), 5.51- 5.63 (m, IH), 5.79-5.90 (m, IH), 7.23 (d, 2H), 7.30 (t, IH), 7.45 (t, 2H), 7.79 (br m, 2H), 7.97 (br s, IH), 8.19 (d, IH). LCMS (method 3): Rt 1.75 min MS (ESI): [M + H]+ = 458.0

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 79463-77-7.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; MOWAT, Jeffrey Stuart; STELLFELD, Timo; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; BRUMBY, Thomas; BARACK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (186 pag.)WO2016/91845; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

79463-77-7, 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 79463-77-7 as follows.

A solution of 5-amino-2-[(pyrrolidin-1-yl)methyl]benzoxazole (200 mg, 0.92 mmol) and diphenylcyanocarbonimidate (263 mg, 1.10 mmol) in isopropyl alcohol (3.5 mL) was stirred overnight at ambient temperature, the resulting white solid product, (Z)-phenyl /V- cyano-/V-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)carbamimidate, was filtered and used directly for the next step (290 mg, 87%).

According to the analysis of related databases, Diphenyl N-cyanocarbonimidate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2008/83354; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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. 79463-77-7.

To a solution of N-(2-dimethylaminoethyl)-2,5-dimethoxybenzene 1,4-diamine hydrochloride (0.05g, 0.143mmol) in distilled water (1mL) was added K2CO3 (0.065g, 0.47mmol). This was diluted with EtOAc (1mL) and diphenylcyano-carbonimidate (0.032g, 0.136mmol) was added. The reaction was stirred at RT for 18h. The precipitate was filtered and washed with minimal EtOAc to give the title compound as a light purple solid (0.015g, 29% yield). 1H-NMR (500 MHz, DMSO-d6) 10.11 (s, 1H), 7.51-7.33 (m, 2H), 7.31-6.98 (m, 3H), 6.81-6.64 (m, 1H), 6.28 (br s, 1H), 4.87 (br s, 1H), 3.85-3.62 (m, 5H), 3.12 (s, 3H), 2.17 (s, 6H) ppm; LC-MS 384.3 (M+H); HPLC 1.9 min(method A).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/46120; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

79463-77-7, name is Diphenyl N-cyanocarbonimidate, belongs to nitriles-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. 79463-77-7

To a solution of heptadecan-9-yl 8-((3-aminopropyl)(8-(nonyloxy)-8- oxooctyl)amino)octanoate (220 mg, 0.3 mmol) in 5 mL 2-propanol was added triethylamine (0.04 mL, 0.3 mmol) followed by diphenyl cyanocarbonimidate (72 mg, 0.3 mmol) and the mixture stirred at rt for two hours. To the reaction mixture was added a 2M dimethylamine solution in THF (0.75 mL, 1.5 mmol) and the resulting solution heated to 75 C for 18 hours. Additional 2M dimethylamine/THF solution (0.75 mL, 1.5 mmol) was added and the temperature increased to 85 C. After six hours the reaction was complete by LC/MS so the solution was reduced under vacuum, diluted with DCM and washed once with a saturated aqueous sodium bicarbonate solution. The organic phase was dried (MgSC^), filtered and the filtrate evaporated in vacuo. The residue was purified by silica gel chromatography (0-50% (mixture of 1 % NH4OH, 20% MeOH in dichloromethane) in dichloromethane) to give heptadecan-9-yl (Z)-8-((3-(2-cyano-3,3-dimethylguanidino)propyl)(8-(nonyloxy)-8- oxooctyl)amino)octanoate (119.2 mg, 0.14 mmol, 49%) as a colorless syrup. UPLC/ELSD: RT = 3.52 min. MS (ES): m/z (MH+) 819.0 for C49H95N5O4. XH NMR (300 MHz, CDC13) delta: ppm 7.62 (br. s., 1H); 4.86 (quint, 1H, J = 6 Hz); 4.05 (t, 2H, J = 7.5 Hz); 3.68 (d, 2H, J= 3 Hz); 2.99 (s, 6H); 2.59 (br. s, 2H); 2.43 (br. s, 3H); 2.28 (m, 4H); 1.71 (br. s, 2H); 1.62 (m, 8H); 1.49 (m, 5H); 1.26 (br. m, 50H); 0.88 (t, 9H, J = 7.5 Hz).

Statistics shows that 79463-77-7 is playing an increasingly important role. we look forward to future research findings about Diphenyl N-cyanocarbonimidate.

Reference:
Patent; MODERNATX, INC.; BENENATO, Kerry, E.; KUMARASINGHE, Ellalahewage, Sathyajith; CORNEBISE, Mark; (305 pag.)WO2017/49245; (2017); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts