The 1H and 13C NMR spectra of the compounds were recorded on a Bruker Avance 300 NMR spectrometer operating at 7.05 Tesla magnetic field, controlled by TopSpin 1.3 software package, equipped with 5 mm 1H/13C dual inverse Z-grad probehead, and in DMSO‑d6 solution at 30 °C. The chemical shifts are referred to tetramethylsilane (δTMS = 0 ppm). The chemical structures of the compounds were proven based on two dimensional zqs-TOCSY [20 ], zqs-easy-ROESY [[20] , [21] (link), [22] (link)], multiplicity-edited HSQC as well as HMBC spectra. The LC-MS analyses were performed with Waters liquid chromatograph - mass spectrometer (mass detector, Waters SQD; UV detector, Waters 996 DAD; separation module, Waters Alliance 2795; column, Waters XBridge C18 50 × 4.6 mm 3.5 μm; and the gradient used with solvent-1, water (Mili-Q) containing 0.1% formic acid (Riedel- DeHaen, extra-pure), and solvent-2, acetonitrile (Riedel- DeHaen). The flow-rate was 2 ml/min with 5 μg sample. The MS parameters were used as: Ionisation, ES+/ES-; source block temperature, 110 °C; desolvation temperature, 250 °C; desolvation gas, 500 L/h; cone gas, 80L/h; capillary voltage, 3000 V; cone voltage, 30 V; extractor voltage, 6 V; Rf lens Voltage, 0.1 V; Scan: 80–1000 m/z in 1 s; and Inter-scan delay, 0.1 s.
Xbridge c18 50
Manufactured by Waters Corporation
The XBridge C18 50 is a reverse-phase high-performance liquid chromatography (HPLC) column designed for a wide range of applications. It features a 50 mm length and an internal diameter of 2.1 mm, with a particle size of 3.5 μm. The column is packed with a C18 stationary phase material.
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Lab products found in correlation
3 protocols using xbridge c18 50
1
Structural Elucidation of Compounds by NMR and LC-MS
2
Synthesis of Substituted Piperazine Derivative
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tert-Butyl 4-(2-chloro-6-cyanopyridin-4-yl)piperazine-1-carboxylate
(41 , 1.00 g, 3.10 mmol), (S)-1,3-dimethylpiperazine
(0.99 g, 8.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (141.9
mg, 0.154 mmol), xantphos (184.8 mg, 0.31 mmol), cesium carbonate
(2.02 g, 6.20 mmol), and dry dioxane (8.0 mL) were combined and stirred
in a closed vessel under an argon atmosphere for 16 h at 110 °C.
Brine was added to the mixture, and the product was extracted with
DCM. The combined organic phases were dried, filtered, and concentrated
under reduced pressure. The crude product was purified via preparative
RP HPLC (Gilson, Waters XBridge C18 50 × 150 mm 10 μm,
30 to 98% MeCN in basic water), yielding 240 mg (19%) of42 as an off-white solid.
1H NMR (DMSO-d6, 500 MHz): δ 2.76 (td, 1H, J =
2.8, 11.8 Hz), 2.6–2.7 (m, 2H), 2.5–2.6 (m, 2H), 2.11
(s, 3H), 1.77 (dt, 1H, J = 3.2, 11.0 Hz), 1.44 (t,
1H, J = 10.1 Hz), 0.90 (d, 3H, J = 6.3 Hz).
(
(0.99 g, 8.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (141.9
mg, 0.154 mmol), xantphos (184.8 mg, 0.31 mmol), cesium carbonate
(2.02 g, 6.20 mmol), and dry dioxane (8.0 mL) were combined and stirred
in a closed vessel under an argon atmosphere for 16 h at 110 °C.
Brine was added to the mixture, and the product was extracted with
DCM. The combined organic phases were dried, filtered, and concentrated
under reduced pressure. The crude product was purified via preparative
RP HPLC (Gilson, Waters XBridge C18 50 × 150 mm 10 μm,
30 to 98% MeCN in basic water), yielding 240 mg (19%) of
1H NMR (DMSO-d6, 500 MHz): δ 2.76 (td, 1H, J =
2.8, 11.8 Hz), 2.6–2.7 (m, 2H), 2.5–2.6 (m, 2H), 2.11
(s, 3H), 1.77 (dt, 1H, J = 3.2, 11.0 Hz), 1.44 (t,
1H, J = 10.1 Hz), 0.90 (d, 3H, J = 6.3 Hz).
3
Synthesis of Benzothiophene-4-Carbonyloxy Carbamate
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A mixture of tert-butyl
4-{2-[(Z)-N′-[(Z)-(4S)-2-amino-3-cyano-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carbonyloxy]carbamimi-doyl]-6-[(2S)-2,4-dimethylpiperazin-1-yl]pyridin-4-yl}piperazine-1-carboxylate
(44 , 120 mg, 0.184 mmol) and DBU (140 mg, 0.92 mmol)
was stirred at 90 °C for 16 h. The reaction mixture was diluted
with water, extracted with EtOAc, and the combined organic layers
were washed with brine, dried, filtered, and concentrated. The crude
product was purified via NP chromatography (MeOH/DCM) followed by
preparative RP HPLC (Gilson, Waters XBridge C18 50 × 150 mm 5
μm, 40–98% MeCN in basic water), yielding 65 mg (56%)
of45 as a light brown solid.
1H NMR
(DMSO-d6, 400 MHz): δ 7.08 (s, 2H),
6.89 (s, 1H), 6.18 (s, 1H), 4.5–4.6 (m, 1H), 4.08 (br d, 1H, J = 13.4 Hz), 3.45 (br s, 4H), 2.99 (dt, 1H, J = 3.0, 12.4 Hz), 2.83 (br d, 1H, J = 10.1 Hz),
2.7–2.7 (m, 1H), 2.19 (s, 3H), 2.0–2.1 (m, 2H), 1.8–2.0
(m, 4H), 1.78 (s, 3H), 1.42 (s, 9H), 1.13 (d, 3H, J = 6.6 Hz).
4-{2-[(Z)-N′-[(Z)-(4S)-2-amino-3-cyano-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carbonyloxy]carbamimi-doyl]-6-[(2S)-2,4-dimethylpiperazin-1-yl]pyridin-4-yl}piperazine-1-carboxylate
(
was stirred at 90 °C for 16 h. The reaction mixture was diluted
with water, extracted with EtOAc, and the combined organic layers
were washed with brine, dried, filtered, and concentrated. The crude
product was purified via NP chromatography (MeOH/DCM) followed by
preparative RP HPLC (Gilson, Waters XBridge C18 50 × 150 mm 5
μm, 40–98% MeCN in basic water), yielding 65 mg (56%)
of
1H NMR
(DMSO-d6, 400 MHz): δ 7.08 (s, 2H),
6.89 (s, 1H), 6.18 (s, 1H), 4.5–4.6 (m, 1H), 4.08 (br d, 1H, J = 13.4 Hz), 3.45 (br s, 4H), 2.99 (dt, 1H, J = 3.0, 12.4 Hz), 2.83 (br d, 1H, J = 10.1 Hz),
2.7–2.7 (m, 1H), 2.19 (s, 3H), 2.0–2.1 (m, 2H), 1.8–2.0
(m, 4H), 1.78 (s, 3H), 1.42 (s, 9H), 1.13 (d, 3H, J = 6.6 Hz).
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