Xb c18

Manufactured by Hill-Rom

The XB-C18 is a laboratory column for liquid chromatography. It is designed for the separation and purification of a variety of compounds. The column features a C18 stationary phase, which is commonly used for the analysis of small organic molecules. The technical specifications and performance characteristics of the XB-C18 are available upon request.

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Lab products found in correlation

Prep hplc, by Hill-Rom (7 mentions) Am 400 spectrometer, by Bruker (3 mentions) Hplc system, by Thermo Fisher Scientific (2 mentions) Rp c18 f254 plates, by Merck Group (2 mentions) Thrombin, by Siemens (1 mentions) Dade actin activated cephaloplastin reagent, by Siemens (1 mentions) Vertex 70 spectrometer, by Bruker (1 mentions) Ca 7000, by Sysmex (1 mentions) Cary 50, by Jasco (1 mentions) Lc ltq orbitrap xl spectrometer, by Thermo Fisher Scientific (1 mentions) Vertex 70, by Bruker (1 mentions) Silica gel, by Merck Group (1 mentions) Sephadex lh 20, by Merck Group (1 mentions) Vertex 70 instrument, by Bruker (1 mentions) Ltq xl spectrometer, by Thermo Fisher Scientific (1 mentions) Sephadex lh 20, by GE Healthcare (1 mentions) Silica gel, by Qingdao Marine Chemical (1 mentions)

33 protocols using xb c18

Synthesis of N-(1-Methylpiperidin-4-yl)-4-(4-(Piperidin-4-ylamino)-1,6-Naphthyridin-2-yl)Benzamide

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Example 65

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The solution of tert-butyl 4-(2-(4-(1-methylpiperidin-4-ylcarbamoyl)phenyl)-1,6-naphthyridin-4-ylamino)piperidine-1-carboxylate (16.3 mg, 0.03 mmol) in TFA/DCM (1 mL/5 mL) was stirred at room temperature for 2 hrs. The solution was concentrated and purified by Prep-HPLC (Welch, XB-C18, 21.2 mm×250 mm, 10 um, eluting with 20% CH₃CN in 1‰ TFA in H₂O) to give N-(1-methylpiperidin-4-yl)-4-(4-(piperidin-4-ylamino)-1,6-naphthyridin-2-yl)benzamide (7 mg, 52.5%) as white solid. HPLC/UV purity: 100%; LC-MS (ESI): 445.2 (M+1). ¹H NMR (METHANOL-d₄) δ: 9.58 (s, 1H), 8.58 (d, J=6.0 Hz, 1H), 8.15 (d, J=8.4 Hz, 2H), 8.00 (d, J=8.8 Hz, 2H), 7.80 (d, J=6.0 Hz, 1H), 7.14 (s, 1H), 4.63-4.60 (m, 1H), 3.99-3.95 (m, 1H), 3.30-3.15 (m, 2H), 2.99-2.87 (m, 4H), 2.35 (s, 3H), 2.22 (t, J=12.4 Hz, 4H), 2.06-1.96 (m, 2H), 1.78-1.69 (m, 4H).

US11066420B2. Inhibitors of low molecular weight protein tyrosine phosphatase (LMPTP) and uses thereof (2021-07-20). Sanford Burnham Prebys Medical Discovery Institute [US]. Inventors: Anthony B. Pinkerton [US], Robert J. Ardecky [US], Jiwen Zou [US].

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Synthesis of Naphthyridin-2-yl Indole Derivative

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Example 82

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The mixture of 1-methyl-5-(4-(4-(piperidin-1-ylmethyl)benzylamino)-1,6-naphthyridin-2-yl)-1H-indole-2-carboxylic acid (56 mg, 0.11 mmol), 1-methylpiperazine (22 mg, 0.22 mmol), HATU (62 mg, 0.16 mmol) and DIPEA (42 mg 0.33 mmol) in DMF (1 mL) was stirred at room temperature overnight. Water (30 mL) was added, and then the mixture was extracted with EA (20 mL×3). The combined organic layers were washed with water (20 mL×3) and brine (20 mL×1), dried over Na₂SO₄, filtered and concentrated. The residue was purified with Prep-HPLC (Welch, XB-C18, 21.2 mm×250 mm, 10 um, eluting with 40% CH₃CN in 1‰ TFA in H₂O) to afford (1-methyl-5-(4-(4-(piperidin-1-ylmethyl)benzylamino)-1,6-naphthyridin-2-yl)-1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone (9 mg, 14%) as a TFA salt. HPLC/UV purity: 98%; LC-MS (ESI): 588.3 (M+1)⁺. ¹H NMR (METHANOL-d₄) δ: 9.78 (s, 1H), 8.90 (d, J=5.7 Hz, 1H), 8.31 (s, 1H), 7.96 (d, J=6.0 Hz, 1H), 7.81 (d, J=8.9 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.62-7.68 (d, J=7.8 Hz, 2H), 7.53-7.60 (d, J=7.8 Hz, 2H), 7.15 (s, 1H), 7.02 (s, 1H), 5.06 (s, 2H), 4.29 (s, 2H), 3.94 (s, 3H), 3.53-3.71 (m, 2H), 3.35-3.52 (m, 4H), 3.33-3.34 (m, 4H), 3.00 (s, 3H), 2.94 (t, J=11.7 Hz, 2H), 1.90 (d, J=14.4 Hz, 2H), 1.81 (d, J=12.8 Hz, 1H), 1.65-1.77 (m, 2H), 1.41-1.54 (m, 1H).

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Synthesis of 5-(4-(Methylamino)-1,6-naphthyridin-2-yl)-N-(3-(piperidin-1-yl)propyl)-1H-benzo[d]imidazole-2-carboxamide

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Example 30

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The mixture of 5-(4-chloro-1,6-naphthyridin-2-yl)-N-(3-(piperidin-1-yl)propyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-2-carboxamide (120 mg, 0.2 mmol), and methyl amine (0.5 mL, 1.0 mmol, 2 M THF solution) in DMA (3 ml) was heated to 100° C. and held for 18 hrs. The reaction mixture was poured into water (20 mL), extracted with EA (10 mL×3), the combined organic layers were washed by water and brine, dried over Na₂SO₄. The drying agent was filtered off and the filtrate was concentrated under the reduced pressure to get the residue, which was dissolved in TFA (1 mL) and DCM (10 mL), then stirred at rt for 18 hrs. The solvent was removed under the reduced pressure to get the residue which was purified with Prep-HPLC (Welch, XB-C18, 21.2 mm*250 mm, 10 um, eluting with 40% CH₃CN in 1‰ TFA in H₂O) to afford 5-(4-(methylamino)-1,6-naphthyridin-2-yl)-N-(3-(piperidin-1-yl)propyl)-1H-benzo[d]imidazole-2-carboxamide. (30 mg, 39% yield) as a TFA salt. LC-MS (ESI): 444 (M+1)⁺. ¹H NMR (CD₃OD) δ 9.64 (s, 1H), 8.88 (d, J=6.0 Hz, 1H), 8.40 (s, 1H), 7.90-7.98 (m, 3H), 7.19 (s, 1H), 3.58-3.61 (m, 4H), 3.35 (s, 3H), 3.22-3.26 (m, 2H), 2.96-2.99 (m, 2H), 2.11-2.14 (m, 2H), 1.97-2.01 (m, 2H), 1.80-1.85 (m, 3H), 1.50-1.54 (m, 1H).

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Synthesis of (E)-N-(2-(dimethylamino)ethyl)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylamide

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Example 119

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The solution of 3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylic acid (62 mg, 0.1 mmol), N¹,N¹-dimethylethane-1,2-diamine (18 mg, 0.3 mmol), HATU (114 mg, 0.3 mmol) and DIPEA (58 mg, 0.45 mmol) in DMF (3 mL) was stirred at room temperature overnight. Then 100 mL water was added and the mixture was extracted with EA (100 mL), washed with brine, dried over Na₂SO₄, concentrated and purified by Prep-HPLC (Welch, XB-C18, 21.2 mm×250 mm, 10 um, eluting with 20% CH₃CN in 1‰ TFA in H₂O) to give (E)-N-(2-(dimethylamino)ethyl)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylamide (40 mg, 41.9%) as white solid. HPLC/UV purity: 100%; LC-MS (ESI): 486.8 (M+1)⁺. ¹H NMR (METHANOL-d₄) δ: 9.74 (s, 1H), 8.89-8.89 (m, 1H), 8.10 (d, J=8.4 Hz, 2H), 7.93-7.85 (m, 3H), 7.70 (d, J=15.6 Hz, 1H), 7.27 (s, 1H), 6.84 (d, J=16 Hz, 1H), 3.86 (t, J=6.8 Hz, 2H), 3.74 (t, J=6.8 Hz, 2H), 3.62-3.58 (m, 2H), 3.40-3.36 (m, 2H), 3.36-3.30 (m, 2H), 3.00 (s, 6H), 2.97-2.94 (m, 2H), 2.34-2.30 (m, 2H), 1.99-1.95 (m, 2H), 1.87-1.78 (m, 3H), 1.59-1.49 (m, 1H).

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Synthesis of Naphthyridin-2-yl Acrylamide Derivative

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Example 124

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The mixture of (E)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylic acid (205 mg, 0.5 mmol), 2-(4-methyl-1,4-diazepan-1-yl)ethanamine (78 mg, 0.5 mmol), HATU (380 mg, 1 mmol) and DIPEA (129 mg, 1 mmol) in DMF (5.0 mL) was stirred at room temperature overnight. Then 50 mL water was added and the mixture was extracted with EA (200 mL), washed with water (100 mL×2) and brine (100 mL×1), dried over Na₂SO₄, filtered, concentrated and purified by Prep-HPLC (Welch, XB-C18, 21.2 mm×250 mm, 10 um, eluting with 20% CH₃CN in 1‰ TFA in H₂O) to give (E)-N-(2-(4-methyl-1,4-diazepan-1-yl)ethyl)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylamide (100 mg, 36%) as white solid. HPLC/UV purity: 100%; LC-MS (ESI): 556.3 (M+1)⁺. ¹H NMR (METHANOL-d₄) δ: 9.75 (s, 1H), 8.89 (d, J=6.0 Hz, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.93 (d, J=6.0 Hz, 1H), 7.89 (d, J=8.0 Hz, 2H), 7.70 (d, J=16.0 Hz, 1H), 7.28 (s, 1H), 6.84 (d, J=16.0 Hz, 1H), 3.88-3.74 (m, 6H), 3.76 (t, J=5.6 Hz, 2H), 3.66-3.59 (m, 6H), 3.44 (t, J=5.6 Hz, 2H), 3.32-3.30 (m, 2H), 3.01-2.94 (m, 5H), 2.37-2.30 (m, 4H), 1.99-1.95 (m, 2H), 1.88-1.79 (m, 3H), 1.59-1.50 (m, 1H).

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Synthesis of N-(2-(4-methyl-1,4-diazepan-1-yl)ethyl)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)propanamide

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Example 133

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The mixture of 3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)propanoic acid (104 mg, 0.25 mmol), 2-(4-methyl-1,4-diazepan-1-yl)ethanamine (40 mg, 0.25 mmol), HATU (190 mg, 0.5 mmol) and DIPEA (65 mg, 0.5 mmol) in DMF (5.0 mL) was stirred at room temperature for 3 hours. Then 50 mL water was added and the mixture was extracted with EA (100 mL), washed with brine, dried over Na₂SO₄, concentrated and purified by Prep-HPLC (Welch, XB-C18, 21.2 mm×250 mm, 10 um, eluting with 20% CH₃CN in 1‰ TFA in H₂O) to give N-(2-(4-methyl-1,4-diazepan-1-yl)ethyl)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)propanamide (40 mg, 28.7%) as yellow solid. HPLC/UV purity: 100%; LC-MS (ESI): 558.4 (M+1)⁺. ¹H NMR (METHANOL-d₄) δ: 9.81 (s, 1H), 8.82 (d, J=6.0 Hz, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.95 (d, J=6.0 Hz, 1H), 7.58 (d, J=8.4 Hz, 2H), 7.24 (s, 1H), 3.87 (t, J=6.8 Hz, 2H), 3.63-3.58 (m, 2H), 3.42-3.35 (m, 6H), 3.11-3.05 (m, 6H), 2.95-2.88 (m, 6H), 2.76-2.73 (m, 2H), 2.67 (t, J=7.2 Hz, 2H), 2.39-2.33 (m, 2H), 2.11-2.05 (m, 2H), 1.98-1.80 (m, 5H), 1.62-1.50 (m, 2H).

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Analytical Methods for Compound Characterization

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The melting point (uncorrected) was determined on an apparatus made by Beijing TECH INSTRUMENT CO. LTD. Optical rotations were measured with a Perkin Elmer spectropolarimeter. The UV spectra were measured on a VARIAN SARY 50 spectrophotometer. The IR spectra were recorded using a BRUKER VERTEX 70 spectrometer. The NMR experiments were run on a Bruker AM-400 spectrometer. The HRFABMS data were obtained on a VG 7070-HF spectrometer. Column chromatographic separations were carried out using silica gel H60 and ODS as packing materials. HSGF254 silica gel TLC plates were used for analytical TLC. The HPLC columns consisted of a Welch Material column (XB-C18, 10 μm, 10 × 250 mm), a normal phase chiral column (CHIRALPAK AS-H, 10 μm, 4.6 mm × 250 mm, part no. 20325), and a reversed phase chiral column (CHIRALPAK AD-RH, 10 μm, 4.6 mm × 150 mm, part no. 19724). The automatic coagulative instrument (Sysmex CA-7000), activated partial Thromborel S, Thrombin and Dade Actin Activated Cephaloplastin Reagent were commercial reagents from Siemens Healthcare Diagnostics Products GmbH. The semi-automatic biochemical analyser (MC-4000, Germany).

Lei L., Xue Y.B., Liu Z., Peng S.S., He Y., Zhang Y., Fang R., Wang J.P., Luo Z.W., Yao G.M., Zhang J.W., Zhang G., Song H.P, & Zhang Y.H. (2015). Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity. Scientific Reports, 5, 13544.

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Synthesis of N,N-diethyl-5-(4-((3-(piperidin-1-yl)propyl)amino)-1,6-naphthyridin-2-yl)-1H-benzo[d]imidazole-2-carboxamide

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Example 35

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A mixture of N,N-diethyl-5-(4-((3-(piperidin-1-yl)propyl)amino)-1,6-naphthyridin-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-2-carboxamide (100 mg, 0.162 mmol) and TFA (1 mL) in DCM (1 mL) was heated to 40° C. and held for 2 hrs, the solvent was removed under the reduced pressure to get the residue which was purified with Prep-HPLC (Welch, XB-C18, 21.2 mm*250 mm, 10 um, eluting with 20% CH₃CN in 1‰ TFA in H₂O) to afford N,N-diethyl-5-(4-((3-(piperidin-1-yl)propyl)amino)-1,6-naphthyridin-2-yl)-1H-benzo[d]imidazole-2-carboxamide (80 mg, 80%) as a TFA salt. HPLC/UV purity: 100%; LC-MS (ESI): 486 (M+1)⁺. ¹H NMR (CD₃OD) δ 9.73 (s, 1H), 8.87 (d, J=6.1 Hz, 1H), 8.40 (s, 1H), 7.85-8.02 (m, 3H), 7.29 (s, 1H), 4.06 (q, J=7.0 Hz, 2H), 3.85 (t, J=6.9 Hz, 2H), 3.54-3.70 (m, 4H), 3.34 (d, J=3.4 Hz, 2H), 2.96 (t, J=12.4 Hz, 2H), 2.23-2.37 (m, 2H), 1.95 (d, J=14.3 Hz, 2H), 1.69-1.88 (m, 3H), 1.45-1.58 (m, 1H), 1.27-1.35 (m, 6H).

US11731986B2. Inhibitors of low molecular weight protein tyrosine phosphatase (LMPTP) and uses thereof (2023-08-22). Sanford Burnham Prebys Medical Discovery Institute [US]. Inventors: Anthony B. Pinkerton [US], Robert J. Ardecky [US], Jiwen Zou [US].

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Spectroscopic Characterization of Compounds

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Optical rotations were determined with a Perkin-Elmer 341 polarimeter. UV, ECD, and FT-IR spectra were measured using a Varian Cary 50, a JASCO-810 spectrometer, and a Bruker Vertex 70, respectively. NMR spectra were recorded on a Bruker AM-400 spectrometer, and the ¹H and ¹³C NMR chemical shifts were referenced to the solvent or solvent impurity peaks for CDCl₃ (δ_H 7.26 and δ_C 77.0) and pyridine-d₅ (δ_H 7.19 and δ_C 123.5). High-resolution electrospray ionization mass spectra (HRESIMS) were obtained in the positive ion mode with a Thermo Fisher LC-LTQ-Orbitrap XL spectrometer. Semi-preparative HPLC was performed on an Agilent 1200 quaternary system with a UV detector or on a Dionex HPLC system equipped with an Ultimate 3000 pump, an Ultimate 3000 autosampler injector, and an Ultimate 3000 diode array detector (DAD) controlled by Chromeleon software (version 6.80) using a reverse-phase C₁₈ column (5 μm, 10 × 250 mm, Welch Ultimate XB-C₁₈). Column chromatography was performed using silica gel (100–200 and 200–300 mesh; Qingdao Marine Chemical Inc., China), ODS (50 μm, Merck, Germany), Sephadex LH-20 (Merck, Germany), or MCI gel (75–150 μm, Merck, Germany). Thin-layer chromatography (TLC) was performed with silica gel 60 F₂₅₄ (Yantai Chemical Industry Research Institute) and RP-C₁₈ F₂₅₄ plates (Merck, Germany).

Zhu H., Chen C., Tong Q., Chen X., Yang J., Liu J., Sun B., Wang J., Yao G., Luo Z., Xue Y, & Zhang Y. (2015). Hyperisampsins H–M, Cytotoxic Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii. Scientific Reports, 5, 14772.

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Synthesis of Naphthyridine-Based Acrylamide

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Example 121

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The mixture of (E)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylic acid (84 mg, 0.2 mmol), (1-methylpiperidin-4-yl)methanamine (26 mg, 0.2 mmol), HATU (76 mg, 0.2 mmol) and DIPEA (52 mg, 0.4 mmol) in DMF (5.0 mL) was stirred at room temperature overnight. Then 100 mL water was added and the mixture was extracted with EA (100 mL×2), washed with brine, dried over Na₂SO₄, concentrated and purified by Prep-HPLC (Welch, XB-C18, 21.2 mm×250 mm, 10 um, eluting with 20% CH₃CN in 1‰ TFA in H₂O) to give (E)-N-((1-methylpiperidin-4-yl)methyl)-3-(4-(4-(3-(piperidin-1-yl)propylamino)-1,6-naphthyridin-2-yl)phenyl)acrylamide (60 mg, 57%) as yellow solid. HPLC/UV purity: 100%; LC-MS (ESI): 526.9 (M+1)⁺. ¹H NMR (METHANOL-d₄) δ: 9.75 (s, 1H), 8.88 (d, J=6.0 Hz, 1H), 8.08 (d, J=8.4 Hz, 2H), 7.93 (d, J=5.6 Hz, 1H), 7.89 (d, J=8.0 Hz, 2H), 7.67 (d, J=16.0 Hz, 1H), 7.27 (s, 1H), 6.85 (d, J=15.6 Hz, 1H), 3.86 (t, J=6.4 Hz, 2H), 3.62-3.55 (m, 4H), 3.55-3.31 (m, 4H), 3.04-2.94 (m, 2H), 2.93-3.00 (m, 4H), 2.88 (s, 3H), 2.34-2.30 (m, 2H), 2.08-1.79 (m, 7H), 1.58-1.52 (m, 2H).

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