Isonicotinoyl chloride hydrochloride

Manufactured by Merck Group

Sourced in Germany, Canada, United States

Isonicotinoyl chloride hydrochloride is a chemical compound that serves as a precursor for various pharmaceutical and chemical synthesis applications. It is a white crystalline solid that is soluble in organic solvents. The compound is commonly used as a starting material in organic synthesis reactions.

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Hydrochlorides (2 citations)

4 protocols using isonicotinoyl chloride hydrochloride

Synthesis of Pyridine-Containing Compound E55

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Example 55

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E47 (30 mg, 0.060 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 mL, 0.560 mmol) were added to isonicotinoyl chloride hydrochloride (Sigma Aldrich, cat no 228753) (79.66 mg, 0.450 mmol) in DCM (0.560 mL) and stirred for 2 h. Then the mixture was partitioned between water and DCM and concentrated in vacuo. The crude was directly purified by preparative HPLC (H₂O, CH₃CN 0.1% HCOOH). The pure fractions were combined and lyophilized to afford E55 (17.6 mg, 0.033 mmol). ¹H NMR (300 MHz, DMSO-d6+TFA) δ 2.16-2.26 (m, 3H), 2.96-3.12 (m, 1H), 3.14-3.49 (m, 2H), 3.58-4.12 (m, 6H), 4.37-4.72 (m, 2H), 6.94-7.18 (m, 1H), 7.38-7.67 (m, 3H), 7.94-8.12 (m, 2H), 8.37-8.54 (m, 1H), 8.94 (s, 2H), 9.26-9.41 (m, 1H). Method 3: Rt=2.55 min, m/z=514 (M+H)⁺.

US11504382B2. Tricyclic inhibitors of Hepatitis B virus (2022-11-22). Antios Therapeutics, Inc. [US]. Inventors: Raffaele De Francesco [IT], Lorena Donnici [IT], Luca Guidotti [IT], Matteo Iannacone [IT], Romano Di Fabio [IT], Vincenzo Summa [IT], Adolfo Prandi [IT], Pietro Randazzo [IT], Davide Gornati [IT], Alessandro Grillo [IT], Luca Ferrante [IT], Leda Ivanova Bencheva [IT], Marilenia De Matteo [IT], Marco Ferrara [IT].

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Vitamin D Metabolite Derivatization Reagents

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The investigated reagents for the chemical derivatization reactions were PTAD, FMP-TS (< 5% 2-hydroxy-1-methylpyridinium p-toluenesulfonate, technical grade, ≥ 90%), isonicotinoyl chloride hydrochloride (95%), acetic anhydride (≥ 99%), pyridine (anhydrous, 99.8%), acetonitrile (ACN) (anhydrous, 99.8%); 4-dimethylaminopyridine (DMAP) (99%) obtained from Sigma-Aldrich (Steinheim, Germany); acetic acid and triethylamine (≥ 99,5%) from Carl Roth GmbH & Co. KG (Karlsruhe, Germany); DMEQ-TAD from Enzo Life Sciences (City, NY, USA); 2-nitrosopyridine from MedChemExpress (City, NJ, USA); and Amplifex Diene Reagent Kit from Sciex (Darmstadt, Germany).
Standards were purchased as follows: 3β-25(OH)D₃ and 1,25(OH)₂D₃ from Cayman Chemical (Ann Arbor, MI, USA); vitamin D₃ and 24,25-dihydroxyvitamin D₃ ((24R)-24,25(OH)₂D₃) from Toronto Research Chemicals (Toronto, ON, Canada); and 3α-25(OH)D₃ from Sigma-Aldrich (Steinheim, Germany).
Acetonitrile and methanol (MeOH) (UHPLC-MS grade) were obtained from Chemsolute (Th. Geyer GmbH & Co. KG, Renningen, Germany), while formic acid (97%) was from Alfa Aesar (Karlsruhe, Germany). A Millipore (Bedford, MA, USA) Direct-Q8 purification system was used to produce organic free water.
The human vitamin D₃ free serum was purchased from Sigma-Aldrich (VD-DDC Mass Spect Gold serum).

Alexandridou A, & Volmer D.A. (2022). Stability of sample extracts of vitamin D3 metabolites after chemical derivatization for LC–MS/MS analysis. Analytical and Bioanalytical Chemistry, 415(2), 327-333.

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Sensitive Vitamin D Metabolite Quantification

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Standards of 3β-25(OH)D₃ and 1,25(OH)₂D₃ were purchased from Cayman Chemical (Ann Arbor, MI, USA); vitamin D₃ and (24R)-24,25(OH)₂D₃ from Toronto Research Chemicals (Toronto, ON, Canada); 3α-25(OH)D₃, 4-phenyl-1,2,4-triazoline-3,5-dione, 2-fluoro-1-methylpyridinium-p-toluenesulfonate, iso nicotinoyl chloride hydrochloride (95%), nicotinoyl chloride hydrochloride (97%), acetic anhydride (≥ 99%), pyridine (anhydrous, 99.8%), acetonitrile (anhydrous, 99.8%), and 4-dimethylaminopyridine (99%) from Sigma-Aldrich (Steinheim, Germany); acetic acid and triethylamine (≥ 99.5%) from Carl Roth (Karlsruhe, Germany); 4-[2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalinyl)ethyl]-1,2,4-triazoline-3,5-dione from Enzo Life Sciences (NY, USA); 2-nitrosopyridine from MedChemExpress (Monmouth Junction, NJ, USA); Amplifex Diene Reagent Kit from Sciex (Darmstadt, Germany); and 3β-25(ΟΗ)D₃-[26,26,26,27,27,27-d6] monohydrate from IsoSciences (Ambler, PA, USA). UHPLC-MS-grade acetonitrile and methanol were obtained from Chemsolute (Th. Geyer, Renningen, Germany) and formic acid (97%) from Alfa Aesar (Karlsruhe, Germany). Organic-free water was generated by a Millipore (Bedford, MA, USA) Direct-Q8 purification system. Human vitamin D₃-free serum (VD-DDC Mass Spect Gold® serum) was purchased from Sigma-Aldrich.

Alexandridou A., Schorr P, & Volmer D.A. (2023). Comparing derivatization reagents for quantitative LC–MS/MS analysis of a variety of vitamin D metabolites. Analytical and Bioanalytical Chemistry, 415(19), 4689-4701.

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Synthesis of Nitrogen-Containing Heterocycles

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Analytical grade 1-fluoro-2-nitro-4-trifluoromethyl benzene, piperidine, morpholine, cyclohexylamine, diethylamine, 4-bromoaniline, pyrrolidine, iso nicotinoyl chloride hydrochloride, nicotinoyl chloride hydrochloride, 2-chloropyridine-3-carboxylic acid and benzoyl chloride were purchased from Sigma-Aldrich (St. Louis, MO, USA) and used without further purification. Anhydrous tin(II) chloride and triethylamine were purchased from Vetec (Rio de Janeiro, Brazil) and used as received. 1 H NMR and 13 C NMR spectra were recorded on a Varian Mercury 300 instrument (Varian, Palo Alto, CA, USA) at 300 MHz and 75 MHz, respectively, using CDCl 3 and CD 3 OD as solvents. Infrared spectra were recorded on either a Varian 660-IR, equipped with GladiATR scanning from 4000 to 500 cm -1 or a Perkin Elmer Paragon 1000 FTIR spectrophotometer (Perkin Elmer do Brasil Ltda, São Paulo, Brazil), using potassium bromide (1% v/v) disks, scanning from 600 to 4000 cm -1 . Melting points are uncorrected and were obtained with an MQAPF-301 melting point apparatus (Microquimica, Campinas, Brazil). Analytical thin layer chromatography was carried out on TLC plates covered with 60GF254 silica gel. Column chromatography was performed on silica gel (60-230 mesh). Solvents used as eluents were used without further purification.

Teixeira R.R., de Andrade Barros M.V., Bressan G.C., Siqueira R.P., Dos Santos F.S., Bertazzini M., Kiralj R., Ferreira M.M.C, & Forlani G. (2017). Synthesis, theoretical studies, and effect on the photosynthetic electron transport of trifluoromethyl arylamides. Pest management science, 73(11).

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