Category: 14658-93-6

Reference of 14658-93-6, These common heterocyclic compound, 14658-93-6, name is 2-Hydroxy-N,N-dimethylacetamide, 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.

EXAMPLE 9.2 (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-((R)-2-dimethylcarbamoylmethoxycarbonyl-pyrrolidin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate 25 mg (0.08 mmol) TBTU and 11 muL (0.08 mmol) triethylamine were added to a solution of 50 mg (0.07 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-((R)-2-carboxy-pyrrolidin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 1 mL DMF and stirred for 10 min at RT. 8.1 mg (0.08 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added to the reaction mixture and this was shaken overnight at RT. After filtration through a syringe filter the reaction solution was purified by HPLC without further working up. The fractions containing the product were combined and freeze-dried. Yield: 38 mg (68% of theory) ESI-MS: (M+H)+=820/822 (Cl)

The synthetic route of 14658-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mueller, Stephan Georg; Rudolf, Klaus; Lustenberger, Philipp; Schaenzle, Gerhard; Santagostino, Marco; Stenkamp, Dirk; Arndt, Kirsten; Doods, Henri; US2007/49581; (2007); A1;,
Amide – Wikipedia,
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Synthetic Route of 14658-93-6, These common heterocyclic compound, 14658-93-6, name is 2-Hydroxy-N,N-dimethylacetamide, 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.

6.2a) dimethylcarbamoylmethyl 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]propionyl}-1,4′-bipiperidinyl-4-carboxylate 30 mg (0.29 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added at RT to a solution of 200 mg (0.25 mmol) 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4′-bipiperidinyl-4-carboxylic acid (Example 6.1a), 90 mg (0.28 mmol) TBTU and 80 muL (3.73 mmol) triethylamine in 1.8 mL DMF and this was stirred for 20 h at RT. The reaction mixture was poured onto saturated NaHCO3 solution, the precipitate formed was suction filtered and dried. Further purification was carried out by HPLC, the fractions containing the product were combined and lyophilised. Yield: 100 mg (47% of theory) ESI-MS: (M+H)+=851 Retention time (HPLC-MS): 3.9 min (method B)

The synthetic route of 14658-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mueller, Stephan Georg; Rudolf, Klaus; Lustenberger, Philipp; Stenkamp, Dirk; Santagostino, Marco; Paleari, Fabio; Doods, Henri; Arndt, Kirsten; Schaenzle, Gerhard; US2007/72847; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 14658-93-6, 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 14658-93-6 as follows.

General procedure: A solution of 0.04 g (0.11 mmol) of methyl 2-Z-(C-(bromomethyl)-N-tetrahydropyran-2-yloxy-carbonimidoyl)pyridine-4-carboxylate (Intermediate 12) in 0.5 mL of dry THE was added drop wise at 0C and under nitrogen atmosphere to a suspension of 0.024 g (0.13 mmol) of tert-butyl N-(2-hydroxyethyl)-N-methyl-carbamate and 0.0054 g (0.13 mmol) of NaH (60% mineral oil) in 0.5 mL of dry THE. Once the addition was complete, the reaction mixture was quenched with 5% citric acid and extracted with DCM and DCM/MeOH90:10. The combined organic layers were dried, concentrated and the crude product was purified by flash chromatography (eluent DCM:MeOH 97:3) to afford 0.022 g (27%) of 2- [(Z)-C-[2-(tert-butoxycarbonyl (methyl )am ino)ethoxymethyl]-N-tetrahydropyran-2-yloxy- carbonimidoyl]pyridine-4-carboxylic acid (Intermediate 19). MS (ESI): mlz: 436 [M-H].

According to the analysis of related databases, 14658-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IEO – ISTITUTO EUROPEO DI ONCOLOGIA S.R.L.; VARASI, Mario; VILLA, Manuela; TRIFIRO’, Paolo; FANCELLI, Daniele; MERCURIO, Ciro; VIANELLO, Paola; SARTORI, Luca; (202 pag.)WO2017/198785; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics